1. Real Madrid 3-3 Manchester United, 1968 European Cup Semi-Final

(OK, so it wasn’t at Old Trafford, but this is the most important game United ever had against Madrid, and there are only four other home legs, and this column is called top fives. So be quiet.)

Determined to prove his prophecy that preceded Munich, Matt Busby’s new side had won a narrow victory in the first leg and had the task of completing the job in front of over a hundred thousand fans at a packed Bernabeu, without the injured Denis Law. The earlier vow of Busby had given the game a sense of destiny, but it didn’t seem that way when half-time game.

United trailed 3-1, an own-goal all they could get, forced by the emergent Brian Kidd. Madrid were cruising, and the mood in the dressing room was grim. Eventually, Busby was able to rally his men, and in the second half, Sadler’s goal gave them the opportunity of a replay (the away goals rule not yet in force.) Another goal, however, saw them win the tie after Best found Bill Foulkes in the area. United had gone to Madrid and matched them, and the final seemed theirs to lose.

More than anything, that came from the sense that destiny had returned, Foulkes being a survivor of Munich and bagging the winning goal. Well, in some cases. Not for Best, who was later to claim that he hadn’t recognised who he was passing to and would’ve taken the shot on himself rather than play it to Foulkes. Those out of towners just don’t get it.

2. Manchester United 4-3 Real Madrid, 2003 Champions League Semi-Final

It shouldn’t be so that one of the all-time great games involving Manchester United was a futile victory that wasn’t quite enough, but it perhaps typifies the era in which it took place. United were in the middle of a painful reformation that remains controversial even now

People will tell you that the saga over David Beckham dominated the game, but nobody has a right to a monopoly on framing a game like this. Ask any Red and they’ll tell you that this encounter was dominated by Ronaldo (plus ca change.) By the time Beckham was introduced, United were on a kamikaze mission, and they ended up completing it. After scoring two to give United an unlikely comeback, Beckham missed a difficult third and looked around to see Ferguson’s enraged reaction, immediately knowing his time had come.

United’s trophy hopes weren’t the only wreckage at the end – Beckham would leave at the end of the season, the biggest sign that the 1999 side was gone, never to return. That process would be excruciating, and although they ultimately ended in defeat, nights like this, with their brief resonance of the doomed glory of the 1980s. It would be five years before Ferguson claimed his vindication – a heavy price, and for some, still a price too high.

3. Manchester United 2-3 Real Madrid, 2000 Champions League Quarter-Final

Perhaps the most infamous and important game on the list, and the one that finally inspired Ferguson to embark on the lengthy campaign of bridge-burning, golden-goose-slaying and boot-kicking that we now know as 4-5-1. It’s astonishing that such a huge decision was undertaken off the back of this game, because it was utterly indescribable.

Firstly, United got off to a disastrous start thanks to a freak Roy Keane own goal, before meeting two players having the games of their lives, a young Iker Casillas keeping everything out while Fernando Redondo was unstoppable in attack, putting on a glorious display as well as, yes, that. It’s not quite got the elegance of John O’Shea vs. Luis Figo, but there’s no accounting for taste. In between all that, Raul was idiotically shown onto his left foot by Silvestre and predictably curled a belter into the top corner.

A late United comeback was too late to salvage anything, although while most of Old Trafford saw an off-day, a freak catastrophe, Ferguson claimed to see the underlying problems, and identified them as the cavalier spirit that had won him his first cup. Both sides still claim they were right.

4. Manchester United 2-2 Real Madrid, 1957 European Cup Semi-Final

1957 was United’s first ever season in Europe, and Matt Busby’s young team took to the continental stage like Anderson to Haribo, wiping the floor with the Belgian champions, Anderlecht 10-0 in their debut game, before succeeding in getting a 3-0 win over Athletic Bilbao in a game that really did shake the world – so much so that Real Madrid made a phenomenal bid to lure Busby to Spain as their manager.

Even now, playing an in-form Real Madrid in Europe seems an almost otherworldly experience, whether down to the all-white kids under floodlights, the colossal names, or the overwhelming sense of history of the club. In those days, it must have been magnified tenfold, with European football was still in it’s infancy, scouting and dossiers on the opposition unheard of, and every game and trip abroad an alien experience. Notably, this was also the first European game hosted at Old Trafford, United playing at Maine Road for home ties earlier in the competition due to a lack of floodlights at their own ground.

Despite the youth and inexperience of the team, and despite Real Madrid possessing one of the greatest teams in history – probably the greatest – United were far from outclassed, but couldn’t quite get the job done. Busby saw the positives in the tie, declaring that if he could beat Real Madrid, he would win the cup. He was right, but it wouldn’t be with the young team he had then.

5. Manchester United 1-0 Real Madrid, 1968, European Cup Semi-Final

When United have played Madrid, it’s usually been a nervy, tense away leg at the Bernabeu followed by a blockbuster, end-to-end thriller at Old Trafford, and usually to the Spaniards’ benefit. Notably, then, in the one success story for United it was the other way around, edging out Real at home before a thrilling battle at the Bernabeu, more on which later.

This was no disciplined job in the style of United’s victory over Barcelona forty years later. United’s reputation was such that Real Madrid – the Real Madrid of Puskas, Di Stefano, and Gento – had come to defend, fielding a back five in a determination to keep United out. A red tidal wave descended upon them, with Paddy Crerand hitting the post and George Best finding a way through to take the lead, but it was all United could manage.

The victory would eventually prove enough, as United’s support later embarked on their first European away trip in significant numbers. But while the result was a narrow one, it finally showed something more valuable – unlike ten years before, Madrid had come to Old Trafford and were too scared to play. United had arrived as a European giant.




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