The worst of Manchester United

Every club, no matter how successful, has moments in their history that fans remember with disappointment, resignation and, occasionally, utter sadness. Man United is no exception. At one end of the spectrum we have the terrible tragedy of Munich, at the other are cup defeats, poor transfers and the very annoying success of our closest neighbours. See whether you agree with this list of the worst moments in the history of United.

14. The night of the minnow – Grimsby 2-2 United (Grimsby win 12-11 on penalties), Aug 2025

When Harry Maguire headed in an equaliser in the 89th minute, it looked as though United had averted their worst ever defeat in the Carabao Cup. Grimsby Town, a non-league team as recently as 2022, and still only mid-table in Division 2, were the hosts for the second round tie. A second-string United dominated possession but were largely toothless in attack, and mistakes at the back, particularly from hapless keeper, Andre Onana, had allowed Grimsby to take a 2-0 lead at half time.

Changes made by Amorim to strengthen his side at half-time had some impact, but it took until the 75th minute for substitute Bryan Mbeumo to halve the deficit. Maguire’s equaliser then took the game to penalties, which surely should favour United’s. It certainly looked like it when Clarke Oduor missed Grimsby’s third attempt, leaving Matheus Cunha, one of United’s more convincing new signings, to clinch it for his team with their fifth. Cunha’s effort, however, was weak and easily saved taking penalties to sudden death.

Grimsby’s players were nerveless and all, including their keeper, converted. United kept pace until Bryan Mbuemo whose penalty struck the underside of the bar and bounced away. Grimsby had won an epic shoot-out 12-11 and United had lost to a team three divisions below them.

Five other dismal Cup defeats:

  • United 1-2 Norwich, FA Cup 4th round, Feb 1967 – a team featuring Best, Law, Charlton and Stiles fell to Second Division Norwich
  • United 0-3 York City, League Cup 2nd round first leg, Sept 1995 – a strong United team won the second leg but still went out on aggregate to third tier opposition
  • United 0-1 Leeds, FA Cup 3rd round, Jan 2010 – a top-class finish by Jermaine Beckford won it for third tier Leeds
  • MK Dons 4-0 United, League Cup 2nd round, Aug 2014 – a weakened team were humiliated by League One opponents inspired by a young Dele Alli
  • United 0-1 Southampton, FA Cup final, May 1976 – Second division Southampton had won nothing in their history. Kept in the game by keeper Ian Turner, an 83 min goal from Bobby Stokes clinched it for the Saints

13. The invisible kit – Southampton 3-1 United, April 1996

In April 1996 United were well on their way to a second title in three years, while Southampton were struggling at the other end of the table. The visit to The Dell was expected to be a formality. It was anything but. Southampton went off like a train and utterly dominated the champions-elect. Goals from Ken Monkou, Neil Shipperley and Matt le Tissier (surprisingly his first that season from open play) took the home side into a shock 3-0 lead.

Something had to change, but no-one expected what did change. Alex Ferguson, furious at his team’s abject performance, saw something that others had not. His observation was that the United away strip was not sufficiently visible in the bright sunshine. The predominantly grey shirts meant that his players could not see each other against the crowd. Lee Sharpe recalls it thus: “The manager just stormed in and said ‘Get that kit off, you’re getting changed”.

They appeared, to the bemusement of those watching, for the second half in their second away strip, with blue and white stripes. It didn’t make much difference but United did at least stop the rot and ‘won’ the second half, finishing 1-3 down. United were fined for the change (£10,000) but Ferguson considered it money well spent. It’s unknown what happened to the grey shirts, but suffice to say that United never played in them again.

12. The career-ending tackle – Roy Keane, Alf-Inge Haaland, April 2001

By any measures Roy Keane is one of the greatest United players of all time. The British record transfer (for what now seems a meagre £3.75m) when he joined from Nottingham Forest in 1995, the Irishman established himself as a lynchpin in the side and won 12 major trophies (seven titles, four FA Cups, one Champions League) during his 12 years at the club.

The adjective that perhaps best describes Keane the player is ‘uncompromising’. He had an intense will to win and would do whatever was necessary to beat the opposition. Always aggressive in the tackle, he was not afraid to step over the line from time to time if he judged it necessary (or indeed if he had temporarily lost the plot). His 13 red cards, the equal most in English football, bear witness to this. While United fans may forgive, indeed even value, many of these indiscretions, one that was utterly unacceptable came against Manchester rivals City in April 2001.

The victim was Norwegian journeyman Alf-Inge Haaland. Haaland had come to England in 1993 and played with modest distinction for Forest and Leeds before joining City. He made what proved to be a fatal error in a match for Leeds against United in September 1997. He was tracking Keane as the two chased a ball into the Leeds penalty area. Keane went down in the box and Haaland, feeling that the United man had dived to win a penalty, stood over him angrily calling him a cheat. Keane remained prostrate on the ground while Haaland was shepherded away by his teammates. It turned out that Keane had suffered a bad cruciate ligament injury that would cause him to miss almost a whole season. Keane would not forget or forgive the behaviour of the Norwegian.

They say revenge is a dish best served cold. Come forward almost four years and Haaland, now at City, comes to visit United. The game is of little importance – United already have the title in the bag and City are destined for relegation. But Roy Keane has an agenda. With five minutes to go a loose ball is cleared by Haaland in the City half. Keane, half a second later, follows through on Haaland with studs up connecting just above the Norwegian’s shin. It’s a leg-breaker, a career-ender. It’s not only a red card, in any other sphere it would be a criminal offence.

Incredibly Haaland went on to finish the match, and it was an injury to his other knee, the left, that caused him to retire from the game. Notwithstanding that, the challenge was a sickener, and perhaps the worst aspect about it was Keane’s lack of any contrition. He admitted in his autobiography that he wanted ‘to hurt’ Haaland, and in a later interview he stated “My attitude was, f**k him. What goes around comes around. He got his just rewards. He f***ed me over and my attitude is an eye for an eye.

Haaland, himself, has had some measure of revenge himself in the performances of his son, Erling. The phenomenal Man City forward has made six appearances against United in the Premier League, scoring eight goals and making three assists. Keane, though, probably could not care less.

11. The signing of Antony – Sept 2022

It seems a little invidious to single out a 22-year-old Brazilian who grew up in poverty and just wants to play football, but Antony symbolises two aspects of a deeper malaise at United in recent years – first, the inability to recruit good players at a sensible cost;  second, the inability once we have got them to get the most out of them.

Antony grew up in the favelas of Sao Paulo and was inducted to the Sao Paulo youth academy aged 10. He was no great prodigy but made his first appearance for the senior team aged 18. The day before his 20th birthday he followed the path of many Brazilians over to Europe when he was signed by Ajax of Amsterdam. Here he came under the tutelage of Erik ten Haag and produced two solid seasons in a team that performed strongly at home and in European competition. That was apparently enough for him as, as soon as interest was shown by United, the player effectively downed tools. On 2 September 2022 he signed for United for €95m, the most ever for an Eredivisie player and the third most ever for United (after Paul Pogba and Romelu Lukaku).

Antony’s career at United was one of almost total frustration. He occasionally looked good with his intricate ball skills and tricks, but he was easily defended against, his ball retention was poor and his output in terms of goals and assists was dismal. The phrase ‘show pony’ might have been invented for him. The United team that he played for was weak, but five goals and three assists in 62 Premier League games was simply not enough. If he did have value, neither ten Haag nor Amorim (who never fancied him) failed to realise it. Then, perhaps most annoyingly for United fans, Antony started to look like a decent player once he’d left the club and gone to Real Betis. He’s almost doubled his United goal tally with nine goals in just 26 matches.

Antony may not be the worst United signing in terms of value for money but he must be close. Some other high ticket players who might challenge:

  • Jadon Sancho – €85m, 2021 – brilliant with Borussia Dortmund, awful ever since
  • Rasmus Hojland – €78m, 2023 – still young, and may come good, but what a price
  • Juan Veron – £28m, 2001 – the most expensive transfer in English football at the time, found the Premier League a little too fast-paced
  • Gary Birtles – £1.25m, 1980 – centre forward who failed to score in 25 league appearance in his first season
  • Diego Forlan – £7m, 2002 – another forward who appeared world-class only once he had left United
  • Morgan Schneiderlin £27m, 2015 – the hard working hub of a Southampton team, looked out of his depth at United. At least they got most of their money back when he went to Everton
  • Angel Di Maria – €76m, 2014 – one of the greatest Argentine players of all-time, could not settle in Manchester. Went on to win the World Cup! 
  • Donny van de Beek – £35m, 2020 – another failure from Ajax, not trusted enough by several managers to start

10. The chancer? – Michael Knighton, 1989

My recollections of Michael Knighton and his attempt to buy Manchester United were not entirely positive. Here was an unknown property developer who seemed more interested in showing off his football skills than in actually running a club; who talked a really good game without having the wherewithal to back up his claims. He looked like just one in a long list of egotistical football chancers. It turns out I may have been wrong. Knighton may well have been simply ahead of his time, and just the spur that United needed to turn things around in the late 1980s.

Knighton was a schoolmaster turned property developer who appeared to have made a lot of money in the mid-late 1980s. He spotted an opportunity in football at a time when the domestic game was not generating anything like the incomes it does today and when most clubs were unprofitable. He saw particular potential in Manchester United with its history and huge worldwide fan base, and with a Chairman, Martin Edwards, who was taking a lot of flak from fans after years of underachievement and might be looking to cash in his chips.

So, in August 1989 Knighton made an offer, through his investment company MK Trafford Holdings, to buy Edwards’ majority stake (50.06%) in United. Extraordinarily, given the value that United commands today, the offer that Edwards accepted for his half of the club was just £10m. Knighton also committed to spend a further £10m updating Old Trafford. The deal was made public and before the start of the opening game of the 1989/90 season, at home to Arsenal, Knighton appeared on the pitch dressed in United kit doing keepie-uppies and shooting the ball into the net. If he wanted to demonstrate that he was a genuine football man and fan, he achieved this, although some observers were, to say the least, skeptical.

Unfortunately for MK Trafford, Edwards and his advisers cooled on the deal before it was finalised. Questions were asked as to whether Knighton really could get his hands on the money he had promised. Knighton maintains to this day that between himself and a handful of wealthy backers, the money was not a problem, but he eventually offered to abandon his bid in return for a seat on the United board. He sat on the board for a couple of years before leaving to try his hand again, this time with a smaller club, buying out Carlisle United.

Knighton’s vision of a United worth £150m proved to be a massive underestimate. Today the club is the most valuable in Britain and is valued at around £5Bn. Revenues from broadcasting rights, product licensing, partner sponsorships and match days are immense, and to some extent Knighton predicted them all. Had he completed his takeover he might now be one of the wealthiest people in the UK. Or perhaps not. We’ll never know. Knighton himself seems reasonably content – he now does something far removed from football, spending his time painting, sculpting and writing poetry.

https://www.bbc.co.uk/sport/football/58233755

9. Ho’way 5-0 – Newcastle 5-0 United, Oct 1996

The 1995/96 Premier League season saw United face one of the stiffest challenges that they came up against during their title-winning years. Newcastle United, under the ownership of local industrialist Sir John Hall and the inspirational management of Kevin Keegan, led the league all the way to March, at one point having a 12-point advantage over United. A collapse in form from mid February, including a critical win for United at St James’ Park, meant that United overhauled them, although there was still time for Keegan’s immortal “I would love it” speech (which you can enjoy in the link below).

The following season Newcastle were expected to mount an even stronger challenge after Alan Shearer was signed from Blackburn Rovers. Although they got off to a slow start (Shearer’s debut was a 0-4 defeat to United in the Community Shield) a run of six consecutive victories in the Premier League saw them top of the table when United visited them in October. United themselves had got off to a decent start, only fourth in the league, but unbeaten in nine games.

The match showed the Magpies at their absolute best. The first goal was the unremarkable. Defender Darren Peacock nodded a ball past Schmeichel and Dennis Irwin failed to stop it crossing the line. The second was a worldie from David Ginola, a curling right foot shot from outside the box. In the second half Shearer skinned Irwin on the wing and delivered a pinpoint cross for Les Ferdinand to head powerfully in. Then Shearer got himself on the scoresheet, putting in the rebound after a good shot from Beardsley. Finally, Belgian Philippe Albert produced one of the goals of any season, chipping audaciously over Schmeichel from well outside the box. When the final whistle sounded the score read Newcastle 5 United 0.

It was bad day at the office and things got worse with a shocking 6-3 loss at Southampton then a third defeat in a row, to Chelsea. But Ferguson and United were undaunted, and the team embarked on a long unbeaten run that lasted until the start of March. When the season came to an end, United had comfortably retained their title and although Newcastle were second, it was a distant second. Keegan, perhaps shell shocked after his tussles with Ferguson, had gone and Newcastle were never quite the same again.

Five other desperate defeats in the league:

  • Crystal Palace 4-0 United, May 6 2024 – ten Haag’s makeshift team got beaten up by a side in the bottom half of the table. They did recover though to win the FA Cup final  
  • United 0-5 Liverpool, Oct 24, 2021 – one in a run of results that led to the sacking of Ole Gunnar Solskjaer. Naby Keita, Diogo Jota and a hat-trick for Salah, all in the first 50 minutes
  • United 1-6 Tottenham, Oct 4, 2020 – a short-lived lead cancelled out by goals from Ndombele, Son (2), Kane (2) and Aurier
  • Liverpool 7-0 United, Mar 5, 2023 – a massive bringing down to earth one week after winning the Carabao cup. Amazingly, it was still scoreless after 40 minutes
  • United 1-6 City, Oct 23, 2011 – a doubly dismal result in the year that City dramatically won on the final day. Without this result their goal difference would have been worse than United’s

8. The not-so golden boy – Alex Ferguson / David Beckham, Feb 2003

One of the greatest strengths of Alex Ferguson as a manager was his ability to maintain discipline and control in a dressing room full of some of the biggest egos in the sport. In an era when player power was becoming increasingly prevalent there was never any question as to who was the boss at United, it was Fergie. A tough man in every sense of the word, he could be both physically and verbally intimidating whenever he felt that standards were slipping.

His players were also aware of another important characteristic of the manager, namely that he was utterly unafraid to get rid of them, whoever they were and whatever they had done, if he felt they were no longer on side. Jaap Stam, Ruud van Nistelrooy, Paul Ince and Roy Keane were the sort of players who would be untouchable at other clubs … Ferguson engineered the exit of all of them when they let him down. There was one player, though, who some thought might be immune, David Beckham, a protégé of Ferguson who had grown up with the club since he was 16 years old.

Beckham, of course, was not immune. There had been signs that the manager was concerned about Beckham’s huge media profile and interests, but while Beckham the player was delivering on the pitch it was not a problem. As soon as Beckham’s form showed signs of falling off – as it did after injury in 2002 – Ferguson was on his case.

Things came to a head (literally) in February 2003. United were sitting second in the league behind Arsenal when the two teams were drawn against each other in the fifth round of the FA Cup. In front of 67,000 home fans United lost 0-2. Ferguson felt that Beckham had not tracked back hard enough for one of Arsenal’s goals and was giving him the full ‘hairdryer’ treatment in the dressing room. Beckham made the fatal error of answering back. A furious Fergie lashed out and kicked a boot on the floor (one of Ole Gunnar Solskjaer’s) straight at Beckham. It struck him on the face, giving him a cut just above the eye. Beckham had to be physically restrained from retaliating, but the damage had already been done to the relationship.

United went on to overtake Arsenal and retain the title, with Beckham playing an important role with goals and assists. Nevertheless, Ferguson, once again, was prepared to lose one of his star players, and Beckham was resigned to leaving. By the start of the 20023/04 season United’s galactico was no longer wearing his treasured red shirt, he was instead in the white of Real Madrid.

7. The sending off – Kevin Moran, FA Cup Final 1985

Irishman Kevin Moran was a pretty exceptional sportsman. In his native country he first excelled at Gaelic football, helping his county Dublin win the top trophy in the sport, the All-Ireland Championship in both 1976 and 1977. He then switched to association football where he established himself as one of the best centre backs in the game. He became a fixture at United where he played over 200 games and one of the first names on the team sheet for his national side, the Republic of Ireland.

He is, however, one of those people whose name will be forever associated with a single unfortunate incident. He became in 1985 the first player ever to be sent off in an FA Cup Final. With about 15 minutes left of normal time, Moran upended Everton’s Peter Reid who had seized on a loose United pass and was charging towards the United goal. As the last defender, Moran was sent off for preventing a goal-scoring opportunity, although the challenge itself would have warranted a red card in today’s game.

At the time, Moran felt he had been grossly wronged; “there was no intent on my behalf. Absolutely none. My foot was on the ground, I was going for the ball. I thought I’d got it.”  Once the referee had signalled his decision, Moran’s on-field reaction was furious. The Irishman did though later admit “it was only afterwards, looking at it, I said; ‘Oh, that doesn’t look great.”

Despite losing Moran, United went on to win the final, with a superb individual goal in extra time from Norman Whiteside sealing the victory. Moran’s joy had the edge taken off it somewhat when he was told he was not allowed to collect his winner’s medal. He nevertheless went up the Wembley steps but to no avail. When he did eventually get his medal, United thought it would be nice for him to be presented with it on the Old Trafford pitch, but the FA blocked this as well. All this for what was the only sending off in his football career.

6. Grim and grimmer – The entire 2024/25 season

In February 2024 the Glazer family seemed to signal a desire (long-awaited by many fans) to become less involved in the management of United by selling a 27.7% stake to Sir Jim Ratcliffe, the billionaire British businessman. Ratcliffe’s Ineos had interests across a range of top-class sport and might be able to bring some of their expertise to football. United had shown a glimmer of promise in the previous season by surprising many to win the FA Cup. Could they build on this in 2024/25?

The short answer is no. The season, if not an unmitigated disaster, was disappointing in almost every regard. It began with a loss to their nearest and dearest, City, in the Community Shield, but at least they made it to penalties. The league campaign started falteringly with goals particularly hard to come by from an inexperienced and misfiring attack. A run of five losses in six games in December (the only win was a come-from-behind classic vs City) meant that United ended the year in 14th! The second half of the season was, if anything, even worse (from 1 April to 16 May they won only two points from eight games!) so United finished the season in 15th, their worst league position for over thirty years.

United fared little better in the domestic cup competitions – knocked out in the fifth round of the FA Cup and quarter-final of the EFL Cup – but they did at least enjoy some success in the Europa League. They qualified well from the league phase, then despatched Real Sociedad, Lyon (after a memorable comeback) and Athletic Bilbao to reach the final. Here, though, there was to be more heartache. In the final they faced Spurs, undergoing an even worse domestic season than United (Spurs finished 17th), and the two teams played out possibly the least entertaining, lowest quality European final in history. United fans would have forgiven this had their team come out on top, but the match was to prove the cherry on a very unappetizing cake – United lost 1-0 to end a truly dismal and depressing campaign. There surely cannot be another season as bad as this … can there?  

5. The row over the racehorse – Rock of Gibraltar

In 1901 a dog played an important part in the saving of Newton Heath FC and subsequent creation of Manchester United. Around a century later, another animal, a racehorse, played arguably a more significant role in the history of the club. The horse was Rock of Gibraltar, European Horse of the Year in 2002 and the first horse to claim seven consecutive Group 1 wins in the northern hemisphere.

The horse was co-owned by United manager, Alex Ferguson, and Susan Magnier, wife of Irish business magnate, John Magnier, founder of the hugely successful stud farm, Coolmore. Ferguson and Magnier shared the spoils as the horse won over £1m in prize money, but a dispute arose when the horse was retired and put out to stud in 2002. A horse with the quality and record of Rock of Gibraltar would be expected to command huge stud fees, and these could last for much longer than the horse’s relatively brief racing career.

Ferguson believed that he should be entitled to a proportion of the horse’s stud fees, but Magnier and his business partner, J.P.McManus, claimed that the breeding rights belonged entirely to them. So, Ferguson launched legal proceedings against them. This might have been restricted to a private matter, but for the fact that Magnier and McManus were significant shareholders in Ferguson’s employer Manchester United. They responded to Ferguson’s action by submitting a list of 99 financial questions to the club, and even threatened to take legal action themselves. They also built their stake in the club, through their investment vehicle Cubic Expressions, to just under 30%, possibly to put pressure on United to sack the manager. Ferguson, though, refused to back down and the club backed him.

As the bad blood lingered, an American investor, Malcolm Glazer, saw an opportunity. He had started with a small stake in the club (2.9%) but had steadily built this up to around 30%. With the Ferguson-Coolmore case still rumbling on unresolved, he made an offer to Magnier and McManus to buy their shares. Their relationship with Ferguson soured, the pair accepted and, in one move, Glazer and his family had taken control of the club. Football finance expert Kieran Maguire has suggested that “if that relationship had remained amicable, then Manchester United might not have been sold”.

United fans have been divided over the impact of the Glazers on the club. To some it’s been a disaster, to the others, a catastrophe. Countless protests have been made, season tickets ripped up, even a wholly new team, United FC, created, but the Glazers retain majority control of Manchester United. It seems a little harsh to blame a racehorse for this, but without Rock of Gibraltar it’s eminently possible that the recent history of the club would have been very different.

4. Everybody was kung-fu fighting – Eric Cantona, Selhurst Park, January 1995

Many United fans, indeed many football fans around the world, might have this incident in their list of best United moments, but I’ve included it in this list because it may have cost United the title that season.

The venue was Selhurst Park for a match against Crystal Palace. United, gunning for a historic third title in a row, sat in second place in the Premier League behind the unexpected leaders, Blackburn Rovers. Palace were one of a number of teams in the league who, secure in the knowledge they could not beat United by skill, attempted to rough-house their way to a result. The first half saw a string of heavy, poor tackles, particularly on Eric Cantona, that went unpunished, and led to Alex Ferguson angrily berating referee Alan Wilkie at half time with “Why don’t you do you f***ing job!”.

Wilkie did produce a card early in the second half, but it was for Cantona, finally cracking and kicking out at Palace defender Richard Shaw. It was red and as both sides crowded the referee, Clive Tyldesley on TV commented “Temperatures rising and there’s the red card. That’s the morning headline. Eric Cantona.” Little did he realise that the red card would be but a footnote in the next morning’s headlines.

As the Frenchman left the pitch, he was confronted from the front of the stands by Palace ‘fan’ Matthew Simmons. At his subsequent trial, Simmons claimed, not at all convincingly, that he had shouted “Off! Off! It’s an early bath for you, Mr Cantona” but no-one believed him, least of all the magistrate. His offensive abuse caused Cantona to completely lose his cool and launch a kung-fu kick at Simmons over the advertising hoardings. Not entirely satisfied this had had the desired effect he followed it up with a very tasty right hook.

Cantona was suspended for the rest of the season and also given a two-week prison sentence, later converted into community service. Hios absence from the United side may have cost them the title so he probably regretted the consequences of his action. One suspects, he never regretted the action itself.

https://www.theguardian.com/football/2020/jan/25/eric-cantona-kung-fu-kick-hooligan-25-years-later

3. The return of the King – United 0-1 City, April 1974

The 1970s was not a golden age for United. Expected to kick on after the European Cup triumph of 1968, the club instead started to go backwards. Several of the key squad members were aging and, after a quarter of a century at the helm, the great Matt Busby retired. The team almost got themselves relegated in 1972/73, and the following season looked as though it could be even worse.

After winning two of their first three games, they went on a dismal run which included only three wins in the next 26 games! Although the defence was reasonably solid, they simply could not score – Alex Stepney was joint leading scorer at Christmas with two penalties – and they entered the final run-in entrenched in the relegation zone. A run of 10 points in six games (there were two points for a win in 73/74) in April gave them some hope, but they still needed wins in their last two games to have the best chance of survival. The first of these saw them pitted against their closest rivals, City, at Old Trafford.

The game was no classic and, although there were chances at both ends, the game entered its final 10 minutes scoreless. United badly needed a goal, but an attack down the left was stopped and the ball moved to City’s Colin Bell. He strode upfield then found Francis Lee on the edge of the box. Lee jagged right then threaded a ball back across the United six-yard box. By a cruel twist of fate, the City forward that it found was Denis Law, all-time United legend, but now playing for the sky blues. Law was unable to stop himself instinctively back-heeling the ball past United keeper Stepney to open the scoring.

Law’s celebration was muted to say the least. He understood the significance of the goal for United. The reaction of the United fans was less muted and they mounted a pitch invasion, perhaps trying to get the match abandoned. After repeated incursions, they succeeded, with the referee taking the players off the pitch and stopping the match, but it was to no avail. The result stood and United had been relegated. They would play in the second tier for the first time since before the war. It was a black day for United and perhaps an even blacker day for ‘The King’, Denis Law, whose goal had condemned his former team to their fate.

2. The worst result imaginable – Man City 3-2 QPR, May 2012

For over three decades from the late 1970s there really was only one team in Manchester. Over a 33-season spell, United finished ahead of their city rivals in all but one of them (1990/91 when City finished fifth to United’s sixth). For some of those seasons, City competed a full division below United and for one memorable season they toiled in the third tier. While United were dominating English football, City were at best slightly better than mediocre.

The turning point came on September 1st 2008 when the Abu Dhabi United Group bought a controlling stake in City. A club that was close to bankrupt under the highly dubious ownership of Thaksin Shinawatra (and that had lost their final league game of the 2007/08 season 8-1 to Middlesbrough) was suddenly the richest club in world football. The essence of their strategy quickly became clear … spend, spend, spend. Robinho, Gareth Barry and Bacary Sagna were amongst the marquee signings in year one; Emmanuel Adebayor, Joleon Lescott and, most egregiously, Carlos Tevez from United, in year two; David Silva, Yaya Toure and the hilarious Mario Balotelli in year three. Some worked and many failed, but they struck gold in 2011/12 with the signing of Argentinian Sergio Aguero.

City’s performances improved year on year. 10th in 08/09, then 5th then 3rd. Still behind United (champions, runners-up then champions) but getting closer. The 2011/12 season saw them close in further still. An incredible start to the season – 12 wins, including a 6-1 thrashing of United at Old Trafford, and two draws saw City top the league at Christmas. But United went on a tear after the new year with 34 points out of a possible 36 to regain their rightful place at the summit. A surprise defeat, though, at Wigan and draw at Everton, meant that the April derby assumed massive importance. City won 1-0, deservedly to be fair, and all of a sudden the title was in their control.

In the event, it all came down to the final day. United had perhaps the easier match of the two, away at Sunderland who were already safe from relegation. City were at home against QPR who needed to win to make sure of staying up. Almost all United fans, even those at Sunderland, were glued to the City game. It was a real roller-coaster.

City went 1-0 up through Zabaleta, but conceded a surprise equaliser from Djibril Cisse just after half-time. City were gifted a one-man advantage when ex-player (and all-round nutcase) Joey Barton got himself sent off for violent conduct, but somehow conceded again, to Jamie Mackie in the 66th minute. City attacked and attacked but could not break through. As normal time ended, they still trailed and United looked set for the title. But City had not given it up. In the second minute of added time, they equalised when Edin Dzeko powered in a header from their 18th corner in the match. Then two minutes later a desperate City mounted a final attack. Aguero passed to Balotelli in the box who, although on the floor, managed to return the ball to his teammate. The Argentinian sidestepped an attempted tackle before firing in a near post shot past QPR keeper Paddy Kenny.

The City of Manchester Stadium understandably went wild. The red side of Manchester went deathly quiet. City had captured the title with almost the last kick of the last match.

United still had it in them to capture another title – a parting gift for Alex Ferguson in the following season – but thereafter City would go on to create the sort of records that had previously belonged to United. With their vast wealth, City would no doubt have risen to the top at some point, but it would still have been so much better had Aguero’s shot gone the other side of the post.

1. Munich

The 6th February 1958 marks the darkest day in the history of Manchester United, and arguably of the whole of English football. The lives of 23 people – including eight members of the amazing ‘Busby Babes’ – were lost from injuries suffered in the Munich Air Disaster. It would be tragic in any circumstances, but even more so because the accident could so easily have been avoided.

United had risen, under the leadership of Matt Busby, to be the best team in England. Busby, ably supported by chief scout Joe Armstrong and assistant manager Jimmy Murphy, had built the side very much from the bottom up. The trio identified, recruited and developed young players, then trusted them to perform in the first team. They were rewarded with the First Division title in 1955/56, a title that they retained in 1956/57. The average age of the team was just 22.

United became the first English team to compete in the European Cup. At their first attempt, they made it through to the semis before losing to eventual champions Real Madrid. At their second, in 1957/58 they reached the quarters where they were drawn against Red Star Belgrade, then of Yugoslavia. After beating their opponents 2-1 at home they travelled to Belgrade for the away leg. Three early goals for United were answered by Red Star in the second half but a 3-all draw was enough to see United through to the semis.

After an overnight stay in Belgrade the team set off for home. The club had chartered an Airspeed Ambassador to carry the team, support staff and journalists home, and this aircraft required a mid-journey refuelling stop at Munich. The weather in Munich was particularly poor, with snow falling in sub-zero temperatures, but the pilot and co-pilot felt confident they could continue the flight. At around 2pm they attempted to take off, but encountered a problem (boost surging) that caused them to abort. They tried a second time, but encountered the same issue, so aborted take-off a second time. All passengers disembarked and made their way to the airport terminal, with most expecting the flight to be cancelled until the next day.

A decision, however, was taken by the pilots to make a third attempt. It proved to be a massive and fatal error of judgement. With all the passengers back on board, the plane accelerated along the runway. It never made it off the ground, careering off the runway and smashing at high speed into a nearby house. The wing and part of the tail were torn off, while the fuselage smashed into a fuel-loaded truck that exploded.

Several of the passengers died instantly, others died later from their wounds. Agonisingly, the great Duncan Edwards after a 15-day fight for his life died after his kidneys failed. Matt Busby’s life was also in the balance (he was twice read the last rites while in hospital) but he recovered after over two months in hospital.

Some injured players recovered well enough to resume their careers;  others, such as Jackie Blanchflower and Johnny Perry, survived the crash but never played again;  miraculously, some, notably Bill Foulkes and Harry Gregg, got out of the plane almost unscathed, physically at least, and both acted heroically trying to rescue colleagues from the wreckage. Many of the survivors carried psychological scars throughout their lives.

Perhaps the most incredible survivor of the crash was Manchester United itself. Somehow the club managed to rebuild itself from the depths of sadness and despair. With Busby back at the helm, the side was reconstructed, and within a year they were competitive again. Within a decade they had risen to become the best team in England, twice winning the Division One title and, most poignantly, capturing the European Cup. Munich was an appalling tragedy for all involved and their families, but it may have made Manchester United stronger in the long run.

Below is a roll-call of the 23 people who lost their lives as a result of the crash:  

Players:

  • Geoffrey Bent, 25, a reserve player who need not have made the trip
  • Roger Byrne, 28, club captain and England international
  • Eddie Colman, 21
  • Duncan Edwards, 21
  • Mark Jones, 24
  • David Pegg, 22
  • Tommy Taylor, 26
  • Liam Whelan, 22, another reserve

United staff:

  • Walter Crickmer, club secretary and former manager
  • Tom Curry, trainer
  • Bert Whalley, coach and former United player

Journalists:

  • Alf Clarke, Manchester Evening Chronicle
  • Don Davies, Manchester Guardian
  • George Follows, Daily Herald
  • Tom Jackson, Manchester Evening News
  • Archie Ledbrooke, Daily Mirror
  • Henry Rose, Daily Express
  • Frank Swift, News of the World & former City goalkeeper and England captain
  • Eric Thompson, Daily Mail

Others:

  • Tom Cable, steward
  • Kenneth Rayment, pilot
  • Willie Satinoff, Manchester businessman
  • Bela Miklos, travel agent