Monaco, Porto, Roma, Villarreal and Ajax are among those to feature as UEFA.com recalls the UEFA Champions League's biggest upsets from the knockout stage.
Article top media content
The UEFA Champions League knockout stage has produced some stunning shocks over the years, with the likes of Dynamo Kyiv, Deportivo La Coruña and APOEL brushing off a lack of European pedigree to upset far more illustrious opponents.
UEFA.com takes a trip down memory lane to reflect on some of the biggest upsets of all.
Monaco 0-0 Manchester United
Manchester United 1-1 Monaco (agg: 1-1, Monaco win on away goals)
Following a 0-0 draw in France, Jean Tigana's Monaco ended United's hopes of becoming European champions 30 years on from their maiden success in 1968. David Trezeguet's thunderous early drive unsettled the injury-sapped hosts and though United equalised through Ole Gunnar Solskjær, attack-minded Monaco deserved their away-goals success. "We were fortunate United had players out but that does not diminish the achievement," Tigana concluded.
Real Madrid 1-1 Dynamo Kyiv
Dynamo Kyiv 2-0 Real Madrid (agg: 3-1)
Dynamo Kyiv talisman Andriy Shevchenko put the Ukrainian side ahead in Madrid, and while Predrag Mijatović replied, the striker settled things in the return fixture – his first a rebound after Bodo Illgner saved his penalty, the second a neat touch following Serhiy Rebrov's deft ball over the top. It was perhaps the high-water mark of Dynamo's second golden age under coach Valeriy Lobanovskiy. They lost to Bayern in the semis, then Shevchenko left for AC Milan.
Porto 2-1 Manchester United
Manchester United 1-1 Porto (agg: 2-3)
2003/04, round of 16
Although Roy Keane's dismissal helped Porto win the first leg, United had one foot in the quarter-finals after Paul Scholes fired them in front – only for Costinha to level when goalkeeper Tim Howard could merely parry Benni McCarthy's free-kick. José Mourinho's ensuing run down the touchline to celebrate came to symbolise the shock outcome. "When Costinha scored, I was going crazy," captain Jorge Costa remembered. "Mourinho was going crazy. Everybody was going crazy."
AC Milan 4-1 Deportivo La Coruña
Deportivo La Coruña 4-0 AC Milan (agg: 5-4)
Overwhelmed by the reigning European champions in the first leg, Javier Irureta's team wiped out that three-goal deficit before half-time in Spain, Walter Pandiani, Juan Carlos Valerón and Albert Luque speeding them into a 3-0 lead. Captain Fran then put the game beyond Carlo Ancelotti's Milan after the break. Irureta had promised to walk the pilgrim's trail to Santiago de Compostela "on his knees" if Depor won; he did, albeit on his feet, at the end of the campaign. "A promise is a promise," he said.
Real Madrid 4-2 Monaco
Monaco 3-1 Real Madrid (agg 5-5, Monaco win on away goals)
Outclassed in Madrid, Monaco trailed to a Raúl González strike at Stade Louis II until Ludovic Giuly volleyed them level on the night just before the interval. Fernando Morientes – on loan from Madrid – headed ASM's second and Giuly flicked in the overall winner on 66 minutes. "I didn't see one story in the papers that gave us a chance," Giuly said afterwards. "If you let them have the ball, they can murder you. But we showed that if you can upset their rhythm, you have a chance."
Inter 2-1 Villarreal
Villarreal 1-0 Inter (agg: 2-2, Villarreal win on away goals)
If defeat in Milan checked an 11-game unbeaten Champions League start for Manuel Pellegrini's Yellow Submarine (even after Diego Forlán's first-minute goal at San Siro), Rodolfo Arruabarrena's header nonetheless secured another mighty scalp for the competition debutants back at El Madrigal. Roberto Mancini laid into his Inter side's "stupid" defending, but Villarreal midfielder Alessio Tacchinardi felt victory was deserved, saying: "We showed heart and soul and a greater desire."
Inter 2-5 Schalke
Schalke 2-1 Inter (agg: 7-3)
2010/11 round of 16
Struggling in the Bundesliga, the Royal Blues shook off their travails with a sensational first-leg triumph against the title holders (despite conceding an all-time classic goal to Dejan Stanković in the opening minute). "If someone had said before the match that we would beat Inter by three goals, we would have said they were mad," coach Ralf Rangnick concluded, his team defending diligently and countering effectively to win the return leg too.
Lyon 1-0 APOEL
APOEL 1-0 Lyon (agg: 1-1, APOEL win 4-3 on pens)
2011/12 round of 16
Having worked wonders to make it through the group stage, the Cypriot club promptly took it a step further; Gustavo Manduca scored to level up their tie with Lyon, and Dionisios Chiotis saved from Alexandre Lacazette and Michel Bastos to win the subsequent shoot-out. "We've made history for this country," Manduca said later. "We knew we had only one chance. We didn't know if we would get another opportunity to get [this far] so we had to give everything."
Barcelona 1-1 Atlético
Atlético 1-0 Barcelona (agg: 2-1)
Diego Simeone's side went on to lift their first Spanish title since 1995/96, and take Real Madrid to extra time in the Champions League final, but few expected them to overcome Barcelona – the great club team of the age. A 1-1 Camp Nou draw was followed by a narrow return victory , Koke's fifth-minute volley settling the tie. "Barcelona are spectacular in how they play the ball around and look to tire you out," the match-winner said. "However, we worked very hard and are worthy winners."
Manchester City 5-3 Monaco
Monaco 3-1 Manchester City (agg: 6-6, Monaco win on away goals)
2016/17, round of 16
What is it with Monaco and the Manchester clubs? Radamel Falcao rolled back the years with a first-leg double, though he was upstaged by a young upstart called Kylian Mbappé and a late three-goal blitz that seemed to put Pep Guardiola's City in control. Mbappé, who said the French side played just like "a bunch of mates", began the fightback in the return and Tiemoué Bakayoko's header sealed progress for the surprise package of that season.
Barcelona 4-1 Roma
Roma 3-0 Barcelona (agg: 4-4, Rome win on away goals)
Two own goals had put Roma on the back foot and Luis Suárez's late fourth seemed to have quelled the hope given to the Italian side by Edin Džeko in the first leg. However, Džeko's early goal and a Daniele De Rossi penalty set up a grandstand finish in the rematch and Kostas Manolas headed the 82nd-minute winner for Eusebio Di Francesco's inspired clan. "It was incredible, crazy – I don't know how to describe it," said Džeko. "We did it when definitely nobody believed in us."
Ajax 1-2 Real Madrid
Real Madrid 1-4 Ajax (agg: 3-5)
2018/19, round of 16
Marco Asensio's late first-leg winner had the Merengues closing in on a ninth successive Champions League quarter-final but Hakim Ziyech and David Neres tipped the tie upside down inside 20 minutes in the return, and the outstanding Dušan Tadić and Lasse Schöne doubled down for Erik ten Hag's side. "This should give us extra energy to do even better this season," said Tadić, and his words proved prophetic – Ajax pulled off a giant-killing against Juventus in the next round too.
Manchester City 1-3 Lyon
The COVID-19 pandemic caused the last-eight ties to be single-leg affairs at a neutral venue and this one at the Estádio José Alvalade provided a serious shock. Kevin De Bruyne eased City's nerves after Maxwel Cornet's opener, but Moussa Dembélé came off the bench to score twice and sink the last English club in the competition. "It's a different year, same stuff," said a bemused De Bruyne as European football's biggest prize continued to elude Guardiola's side.
Villarreal 1-1 Juventus
Juventus 0-3 Villarreal (agg: 1-4)
2021/22, round of 16
Dušan Vlahović recorded the quickest ever goal from a starting Champions League debutant with the opener after 33 seconds, but Daniel Parejo rescued a draw for Unai Emery's underdogs. Gerónimo Rulli kept the Yellow Submarine afloat in Turin before Villarreal produced an Italian-style three-goal counter-punch in the closing 12 minutes. "Tonight will go down in history," lauded Rulli. "We had a chance to make history and the side deserve this."