Barcelona's shock quarter-final defeat to Atletico Madrid means it's now 26 years since any team retained the European Cup. FFT's Chris Flanagan investigates where things have gone wrong for a succession of reigning champions...
That was 1990. It was the 12th time in the 35-year history of the European Cup that the competition had been won by the holders. Real Madrid once won it five years in a row, Ajax and Bayern Munich three times in succession.
But in the 26 years since Milan's second triumph, not one club has managed to retain the trophy. Four (Milan 1995, Ajax 1996, Juventus 1997 and Manchester United 2009) were just one victory short, beaten in the final.
Seven have fallen in the semi-finals, while the Barcelona of 2016 were the seventh to succumb in the quarter-finals. On 11 occasions since 1990, the team who knocked out the holders have gone on to lift the trophy.
For the reigning champions, everything that could go wrong usually does. And plenty have found ways to shoot themselves in the foot too...
1. Floodlight failure? Right, we're off...
Milan fancied their chances of winning the European Cup for a third successive year in 1991, until they ran into Marseille in the quarter-finals.
The French side drew 1-1 at San Siro and Milan's brutal tactics in the second leg weren't enough to stop Chris Waddle. The wideman was concussed by one particularly feisty challenge but recovered to put Marseille 2-1 up on aggregate.
That's how it stayed until stoppage time, when some of the floodlights failed at the Stade Velodrome. The referee insisted it was still light enough to complete the match but Milan were having none of it and scarpered, hoping to force a replay.
The Rossoneri refused to return to the field and the match was abandoned, but Milan were thwarted in their hopes of being granted a replay. Marseille were awarded a 3-0 victory and Milan were banned from Europe for the 1991/92 season. Just finish the game next time, lads.
2. "I just whacked him across the backside with the golf club"
What better way to build up to a match against the European champions than with an alcohol-fuelled row ending with one member of the team being attacked with a golf club?
I wasn't going to let it go, especially after a drink. 'That ginger f***** p****, he ain't speaking to me like that,' I said. Our golf clubs were in the lounge and I'd got one out as I was stewing over what Ginge had done
Things got out of hand when the Reds went on a brief training break to Portugal ahead of the last-16 tie with Barça, and perhaps it wasn't exactly surprising that Craig Bellamy was involved. All was going well on a night out, until the mood turned when Bellamy repeatedly insisted that John Arne Riise should sing a song in front of the squad as punishment for missing the Christmas party.
"He got s****y about it, got up and started shouting," Bellamy later recalled in his autobiography. "I wasn't going to let it go, especially after a drink. 'That ginger f***** p****, he ain't speaking to me like that,' I said. Our golf clubs were in the lounge and I'd got one out as I was stewing over what Ginge had done.
"I knew Ginge was sharing with Daniel Agger so I texted him to ask room what he was in. I let myself into the room, Ginge was in bed. I just whacked him across the backside with the club. You couldn’t really call it a swing. It was just a thwack really."
Well that's OK, then. Fast-forward a few days, and Liverpool won 2-1 at Camp Nou. The goalscorers? Bellamy and Riise, the former celebrating his strike by swinging an imaginary golf club. Barcelona won the second leg 1-0, but Liverpool progressed on away goals.
3. Redondo turns United inside out
Football, bloody hell. Manchester United won the Champions League for the first time under Sir Alex Ferguson in 1999 but their attempts to defend the trophy were undone by Real Madrid and one of the most famous pieces of skill in the history of the competition.
United drew 0-0 at the Bernabeu in the first leg of the quarter-finals but a Roy Keane own goal and a strike from Raul put Madrid 2-0 up at Old Trafford before their memorable third. Argentine midfielder Fernando Redondo left Henning Berg spinning in bewilderment with a brilliant backheeled turn on the touchline, before squaring for Raul to net again and seal the tie.
United fans were forced to relive the moment time and again after Redondo's magic was later included in the Champions League's official TV title sequence. Berg probably made sure he tuned in a couple of minutes late.