As every Manchester United fan, and pundit around the world, was sure of, Manchester United breezed past Olympiacos last night to ensure they would get to the quarter finals of the Champions League. Of course, this will lead to a thrilling victory in May, when David Moyes becomes Sir David Moyes, as United beat Bayern Munich 6-0 in the Champions League final. All this is obvious and definitely going to happen, so until then, let’s look back on the most enjoyable Champions League/European Cup quarter-finals that Manchester United have been involved in.

Manchester United 2-3 Real Madrid, 1999/2000

There have been much better and cleverer accounts of this match made, the best by the attractive Rob Smyth in The Blizzard. Despite that, there’s no way that this quarter final can be skipped.

The first leg, at the Bernabeu, or the Camp Nou, or one of those Spanish grounds – they’re all the same – was a 0-0 draw, notable for the excellent performance of Mark Bosnich, the new, improved Peter Schmeichel. You laugh, but there are a couple of similarities, just look here and here. A lack of an away goal is always something to worry about, but against a team with Raul, Fernando Redondo, Same Name Morientes, Roberto Carlos, and one of the worst people in the world, Steve McManaman, it was a particular weakness.

So it proved. Bosnich was injured, and so came in one of United’s best ever reserve keepers, and one of the most nervous first choices, Raimond van der Gouw. It was perhaps not coincidence that Roy Keane then scored his only own goal for Manchester United, betraying the lack of familiarity. Raul scored the second, and then Fernando Redondo laid down a marker for future United legend John O’Shea in how to showboat.

Two goals for United – one brilliant effort from David Beckham and a late penalty from Paul Scholes – gave the impression that United might chase down another impossible victory, but there was no chance. Iker Casillas, only 18, put in a performance that Alex Ferguson could only describe as ‘not normal.’

Manchester United 4-3 Real Madrid 2002/3

As Santiago Solari said about the tie, “I remember us winning the first game comfortably and that we felt, and in fact were, better than them.” And they were. United had been beaten at the Bernabeu, or the Camp Nou, or one of those Spanish grounds – they’re all the same – 3-1, with Ruud van Nistelrooy giving United a glimmer of hope and, this time, an away goal.

Alex Ferguson dropped David Beckham, who only a couple of months ago he’d booted with a boot in a defeat in the FA Cup at Arsenal, and left him on the bench. Ole Solskjaer, now a superior player in almost every respect, and certainly a superior right winger, was chosen ahead of him (it’s worth lamenting just how good Manchester United would have been with Cristiano Ronaldo, Ronaldinho and a fit Solskjaer playing with Wayne Rooney and Van Nistelrooy).

Ronaldo, intermittently fit, showed just how good he was, though. Ryan Giggs said he was ‘on fire’ and if you were a terrible writer, you would claim that he literally set Old Trafford alight that night with his hat-trick. No-one died.

Yes, United scored four, with Beckham coming on as a substitute to replace Juan Sebastian Veron, who had played ahead of him despite having been injured for the previous seven weeks. Beckham scored his usual free-kick, and also got the winner. Ronaldo was Real’s hero and had put in a ridiculous performance, and Beckham had done as much as he could. It certainly showed Madrid what he could do, and he’d be off to join them in the summer, where he and Ronaldo would get on pretty well.

Manchester United 7-1 Roma, 2006/7

Alex Ferguson used to talk about United making it hard for themselves, whereas what might have been slightly truer was that with his tactical tinkering – trying to spring a surprise only to have to be put right in the second half – and with his welcoming of the Glazers, it was often more a case of Ferguson making it hard for his players, and us. But this really was a case of United making it harder than it needed to be. In the first leg, they’d gone down 2-1 against a merely competent Roma side. After half an hour, United were down to ten men when Paul Scholes was sent off for two quickly earned – and Scholes usually really earned them – yellow cards.

Wayne Rooney did well to score an equaliser, but United conceded late on, and were fortunate not to concede more. They were lucky to get away just a goal down, and the mood shifted from optimistic to genuinely concerned.

But Ferguson didn’t always get his tactics wrong. For the second leg, he pulled off a masterstroke, whether it was deliberate or not. Alan Smith, who Liverpool fans treated with their customary dignity when he broke his leg, was chosen to head a 4-2-3-1 formation despite not having started a Premier League match that season. Michael Carrick decided to play unlike Michael Carrick, scoring an important goal for what one assumes must be the only time in his existence, curling in a brilliant shot from distance. Smith then scored his first goal since 19 November 2005, and United decided that it would also be a laugh to score five more, four of them just as good, five of them just as ridiculously enjoyable.

Inter Milan 1-1 Manchester United 1998/9

On the face of it, the result makes this tie seem pretty, as the Australians say, ordinary. Drawing 1-1 after a 2-0 victory at home is a comfortable 3-1 victory, with an away goal advantage. It certainly didn’t seem that comfortable at the time. While the first leg had been a handy result, with David Beckham finally getting the better of Diego Simeone with two excellent assists for Dwight Yorke, and a fairly hefty challenge of his own on the Argentine, things weren’t exactly relaxing in Milan.

Ronaldo started for Inter Milan, having been rumoured to be out of contention with his continuing problems. Before the match, Ferguson had addressed the possibility of deception in a typically nuanced manner, as Daniel Harris described in his excellent book on the treble, The Promised Land:

““When an Italian tells me it’s pasta on the plate, I check under the sauce to make sure,” said Fergie before the game. “There will be a lot of scheming and diving and referee-baiting; they’ll go through the whole Italian repertoire.”

“Maybe Ferguson has done it because he is afraid,” retorted Lucescu. “That is what you have to ask yourself. Surely there can be no other explanation.” It’s unlikely he was still as convinced, when, at full-time, “Ferguson” came onto the pitch to join in the celebra- tions and Gilles Veissière was one of the first men he congratulated, the fine he would later receive for “unnecessary provocation” well worth the £2,155.”

United were able to hold out for the first half, but in the second, Nicola Ventola put Inter a goal up. United were then under pressure, and Inter missed chances and hit the woodwork as they looked for a second which would bring extra time at their home ground. United were on the back foot, not yet playing with the sense of destiny retrospectively applied to the treble season.

But, with the advantage of hindsight, Paul Scholes’ equaliser with two minutes from time assuring qualification to the semi-final makes the bum altogether less squeaky.

Benfica 1-5 Manchester United, 1965/6

As Tim Sherwood tries to become the first Timothy to win a game in Benfica with Spurs tonight, enjoy Manchester United becoming the first foreign team ever to win there.