1) Galatasaray 0-0 Manchester United, second round, 1993-94

Manchester United's return to the European Cup was fiercely anticipated – they had been away since 1969. After winning the Cup Winners' Cup immediately after the return of English clubs to continental competition, in those crazy altruistic and naive days when that was what was done, they were expected to have a suitable go at the Champions League. But in place at the time was a rule limiting the number of foreigners that could be fielded by each club, and though United's squad was largely British and Irish, the restriction applied to all who were either born outside of England, or were not considered "assimilated".

In the first round, this made little difference, with Honved beaten in both legs – though unconvincingly, by a single goal each time. Next, and in order to qualify for the group stages, United were paired with Galatasaray – who, in typical style, it was assumed that they would beat fairly easily. And at the start of the first leg at Old Trafford, this seemed a reasonable supposition, United dashing into a two-goal lead inside the first quarter-hour, before relaxing in the glow of their superiority.

However, it quickly became clear that Gala, with Hakan Sukur, Kubilay Turkyilmaz, Arif Erdem and Tugay Kerimoglu, were actually aware of what football was and able to play it. So United, with Lees Martin and Sharpe at full-back – Paul Parker was injured and Denis Irwin omitted – tottered, conceding three goals in 48 minutes, before Eric Cantona, wearing No9 in the presence of Bryan Robson, equalised with eight minutes remaining.

After all that, it was still expected that United would resolve matters in the second leg. But they found Istanbul rather less equilibrious than they had hoped, Alex Ferguson later reporting "as much hostility and harassment as I have ever known on a football expedition". Steve Bruce narrowly avoided decapitation via a flying brick, 164 supporters were deposited into cells on account of existing, while on the pitch, they were equally impotent, Mark Hughes – perhaps the player who would have embraced the fear with most joy – now the victim of the foreigners rule.

Quite simply, though, the talent was there, United were not prepared for this level or style of competition, eliminated on away goals following a goalless draw. But there remained misery to follow – Cantona was sent off once the game was over, after honestly appraising the performance of a referee, who, five years later, was found guilty of accepting bribes and banned for life. Then, in the tunnel, Cantona was set about by police, which did not go down well with his team-mates. "We had a few who could look after themselves," said Bruce. "We gave as good as we got." It was undoubtedly the highlight of United's performance.

What happened next: United were already nine points ahead at the top of the table, but in their next game conceded twice in the first half away to Manchester City. With Turkish delight thrown into the United end and chants of "two-nil up and fucked it up, Galatasaray" ringing around Maine Road, United, inspired by Cantona, powered back to win 3-2. They then beat Wimbledon and drew with Ipswich, staying top for the rest of the season, and though they lost in the League Cup final, also won the FA Cup.

• Archive: Rob Smyth on that night in Istanbul

2) Gothenburg 3-1 Manchester United, group stages, 1994-95

At the start of 1994-95, United were again felt to be legitimate Champions League contenders. Roy Keane had been fully integrated into the side, they had learned from their experiences the previous season, and were also entered directly into the group stages. Again, they were drawn with Galatasaray, along with Barcelona and IFK Gothenburg, and again, things began unconvincingly but well enough: a home win over Gothenburg followed by another goalless draw in Turkey. But that same night, the Swedes won at home to Barcelona – who responded by drawing at Old Trafford and disbursing a walloping for the ages at the Camp Nou, while Gothenburg were beating by twice by Galatasaray. If United could avoid defeat when the sides met again, a win over Galatasaray would see them through.

Things did not work out that way. Though Eric Cantona returned after serving a five-match ban, Peter Schmeichel and Roy Keane were injured, replaced by Gary Walsh and Brian McClair respectively, and with Lee Sharpe also absent, Simon Davies started on the left wing. But, most tellingly of all, David May – a limited centre-back – played at right-back, where he was duly guzzled by future United Champions League winner, Jesper Blomqvist. On a filthy November night, the Swede gave Gothenburg the lead on 11 minutes, and though Mark Hughes equalised on 64, a minute later, United were behind again, and a penalty from Pontus Kamark confirmed their defeat with 18 minutes still to go – before Paul Ince got himself sent off.

Though United could argue that their campaign had been hamstrung by injury, suspension, and a shortly to be defunct rule, the reality was unavoidable: they had again behaved in appalling fashion at the crucial moment. In particular, their defence, though plenty good enough for the domestic game, was neither pacy enough nor savvy enough to cope with the best attackers.

What happened next: A 0-0 draw at Arsenal was followed by a home win over Norwich and thrashing of Galatasaray – a game in which David Beckham scored his first for the club. Two months later, Eric Cantona remonstrated with a Palace supporter, and the league was consequently lost by a point, the FA Cup final by a goal.

3) Manchester United 0-1 Bayern Munich, quarter-finals, 2000-01

United steadily improved in Europe through the late 90s, particularly in consecutive ties with Juventus. After enduring perhaps the most complete 1-0 thrashing of all-time in September 1995, they performed far more creditably in losing by the same score two months later and progressed to the semi-finals, where they lost away and at home to Borussia Dortmund – on account of cowardice and profligacy respectively.

But this, along with an exit to Monaco on similar terms, convinced Alex Ferguson of the need to attack, so he recruited Jaap Stam for his ability to defend one-on-one, and in 1999, United won the competition.

Two seasons later came a quarter-final with Bayern Munich, and in the home leg, a newly circumspect United were barely able muster a chance. Gone was the fury with which they had pummelled all-comers, and with Dwight Yorke effectively retired and their wingers closely marked – a tactic that first worked for Croatia Zagreb, visitors to Old Trafford the previous season – they offered little penetration. It was little surprise when Paulo Sérgio opened the scoring with four minutes to go.

Then, in the return, Yorke – who had scored a couple of goals against Coventry in the previous game – was preferred to the more suitable Sheringham, and Nicky Butt selected ahead of Luke Chadwick, in place of the absent David Beckham. Within 39 minutes, Bayern were 2-0 up, and though Giggs pulled one back, it was not until the very end that any sort of fightback was threatened. The treble team were finished.

What happened next: United required two penalties to secure a 1-1 draw with Manchester City in the league. With the title already secure, they beat Middlesbrough, before losing each of their last three games, a run not replicated until this season.

4) Manchester United 2-2 Bayer Leverkusen, semi-final, 2001-02

In a bid to win another European Cup, Alex Ferguson broke up a midfield almost guaranteed to deliver the league championship every season. And though adding Ruud van Nistelrooy and Juan Sebastián Véron gave United greater attacking potency and variety, replacing Jaap Stam with Laurent Blanc awarded opposition the same. So United struggled in the league, producing some spectacular football but finding it hard to establish a method that extracted the most from their players, and consequentially failed to become the first side to record four consecutive titles.

But in the Champions League, they were much improved. After a dodgy start, they drew twice with Bayern, before producing one of the finest performances of the Fergie era to eviscerate Deportivo La Coruña – arguably Europe's best side – away from home, then thrillingly finished the job at Old Trafford.

In the semi-final, they played Bayer Leverkusen – who had eliminated Arsenal in the second group stage, followed by Liverpool in the quarter-finals. But even so, they were viewed almost as a bye to the dream final: United v Real Madrid at Hampden Park, where, in 1960, the young Fergie had been captivated by Puskas and pals' 7-3 win over Eintracht Frankfurt. The rock of Gibraltar was moved to tears by the very prospect.

However, rather like Galatasaray in 1992, this Leverkusen side was full of men who, though unknown at the time, would go on to establish themselves as serious players: Michael Ballack, Zé Roberto, Dimitar Berbatov, Lúcio, and Yildiray Basturk. And United were without David Beckham, following his invention of the metatarsal, and also Roy Keane; aiming to play in a final after missing out in 1999, he would be let down, first in his absence and then in his presence.

An own goal gave United the lead on 29 minutes, but they were unable to force a second before Ballack equalised just after the hour, and though a Van Nistelrooy penalty quickly restored the advantage, Oliver Neuville soon squared the tie. Then, in Leverkusen, Keane willpowered another definitive captain's goal, but this time, his team-mates – one of whom he later accused of shaking with nerves – shrunk. Again, Neuville equalised, this time in first-half injury time, and though Diego Forlán almost sneaked a winner, United were deservedly eliminated.

What happened next: Only two games of the season remained, due to the impending World Cup. In the first, United ceded the Premier League trophy by losing at home to Arsenal, before drawing 0-0 at home to Charlton.

5) Lille 1-0 Manchester United, group stages, 2005-06

After 17 years of service, Alex Ferguson awarded himself an extended sabbatical and testimonial, resulting in the arrival of players such as David Bellion, Eric Djemba-Djemba and Kléberson, along with the Glazer family. As such, United failed seriously to compete in the league for three consecutive seasons, but the nadir came in Europe. In 2004-05, they were easily dispatched by Milan, and then, the following year, were drawn in a group with Benfica, Villarreal and Lille. In what may well have been the worst collection of games in the competition's history, they achieved two goalless draws in the first three games – away to Villarreal and at home to Lille – sneaking a win over Benfica in between.

Next came a trip to Paris, played in awful weather in the awful Stade de France. With a midfield comprising Alan Smith and Kieran Richardson, along with Darren Fletcher and Cristiano Ronaldo, United produced a performance of original, exceptional and irredeemable poverty, losing 1-0. This prompted significant numbers among the travelling support to race to the front at full-time, so the players might be immediately apprised of their achievements – uncommon behaviour, post-1990. And though it took a further 0-0 mess with Villarreal followed by defeat in Lisbon to secure their elimination, this game will forever remain a touchstone for the truly revolting.

What happened next: United somehow scrounged a win at home to Chelsea, thanks to a deflection, then won at Charlton and improved steadily through the season. They began the next on a roll that ended only with the sale of Ronaldo, three years, three titles and one Champions League later.

Daniel Harris's new book, The Promised Land, on Manchester United's treble season, is available here