knockout
Football is arguably the pinnacle of entertainment when it comes to club football. It involves the most elite teams in Europe facing off against one another in a bid for the ultimate prize. are by far in the competition's history and will be aiming to wrap up their fifteenth title at Wembley in June 2024. However, even for Los Blancos, it has not always been plain sailing every year. The
Champions League has a habit of throwing a curveball into the mix and, over the years, some of the more lowly teams in Europe have managed to pull off some major upsets in the latter stages of the competition. This article looks at eight of the most shocking results ever seen in the Champions League knockout stages. The ranking of this list has been determined based on how far apart the two teams in question were in the club coefficient rankings (the official system UEFA uses to rank and seed its teams) in the year of the tournament. Every match on this list took place after the Champions League adopted its current format in 1992. Greatest Shocks of the Champions League Knockout Stages 1 APOEL vs Lyon R16 2012 1-1 (4-3 on penalties) 2 Monaco vs
Manchester City R16 2017 6-6 (away goals) 3 AS Roma vs
Barcelona QF 2018 4-4 (away goals) 4 Ajax vs
Real Madrid R16 2016 5-3 5 Dynamo Kyiv vs Real Madrid QF 1999 3-1 6 Schalke vs Inter Milan QF 2011 7-3 7 Villareal vs Inter Milan QF 2006 2-2 (away goals) 8 Porto vs
Manchester United R16 2004 3-2 Porto's 2004 Champions League triumph under up-and-coming young manager is one of the competition's greatest ever stories. When the Portuguese side were pitted against Sir Alex Ferguson's formidable in the round of 16, most people tipped Porto for an early exit even after Benni McCarthy's brace had seen them win the first leg 2-1 in Portugal. In the return leg at Old Trafford, Paul Scholes' header looked like it was going to be enough to send the Red Devils through on away goals, but right at the death, McCarthy's fierce free-kick was fumbled by United goalkeeper Tim Howard and Costinha was on hand to tap home the rebound and book his side's place in the quarter-finals. The goal caused Mourinho to sprint down the touchline in jubilation and on his first introduction to English football mere months before he was appointed manager. Porto vs Manchester United (3-2 on aggregate) 25 February 2004 Porto 2-1 Manchester United Benni McCarthy (29', 78') Quinton Fortune (14') 9 March 2004 Manchester United 1-1 Porto Paul Scholes (32') Costinha (90') Just seven years after reaching La Liga for the very first time, Villarreal had qualified for the Champions League and made it as far as the quarter-finals where they met Inter Milan, who were on their way to convincingly winning Serie A that season. It looked like being the end of the road for the plucky Spanish side, especially after they were beaten 2-1 at the San Siro in the first leg. However, the Yellow Submarine rallied in the second leg at El Madrigal and defender Rodolfo Arruabarrena's header in the 58th minute was the game's only goal and saw the Spanish side triumph over a star-studded Inter team and progress to the semi-finals on away goals. Villarreal's miraculous run in their very first Champions League campaign finally came to an end in the semi-final when across two legs by . Villarreal vs Inter Milan (2-2 on aggregate) 29 March 2006 Inter Milan 2-1 Villarreal Adriano (7'), Obafemi Martins (54') Diego Forlan (1') 4 April 2006 Villarreal 1-0 Inter Milan Rodolfo Arruabarrena (58') N/A Inter Milan were victims of an even greater upset five seasons later, in a Champions League campaign they entered as defending champions. The Italian giants had unconvincingly qualified out of their group under new manager Rafael Benitez, who had been sacked and replaced by Leonardo by the time Inter incredibly managed to come from behind and knock out in the round of 16. Off the back of an incredible win, the Nerazzurri were strong favourites for their quarter-final match-up with Schalke, but were left stunned as the German side ran riot at the San Siro and won the first leg 5-2. Ralf Rangnick's side progressed to the semi-finals of the Champions League for the first time in their history after also winning the second leg in Gelsenkirchen, but the last four was a step too far, and they were with the eventual aggregate score reading 6-1 to the Red Devils. Schalke vs Inter Milan (7-3 on aggregate) 5 April 2011 Inter Milan 2-5 Schalke Dejan Stankovic (1'), Diego Milito (34') Joel Matip (17'), Edu (40', 75'), Raul (53'), Andrea Ranocchia (57' og) 13 April 2011 Schalke 2-1 Inter Milan Raul (45'), Benedikt Howedes (81') Thiago Motta (49') Dynamo Kyiv were once a regular in the Champions League's latter stages, thanks in no small part to their attack being spearheaded by Andriy Shevchenko at the peak of his powers. Despite this, there weren't many who gave them a chance of getting past holders Real Madrid in the quarter-finals of the 1999 edition. However, the Ukrainian side managed to hold their own and earn a 1-1 draw with Los Blancos at the Santiago Bernabeu before beating them 2-0 in the return leg as Shevchenko bagged a second-half brace. It was the third time in their history that Dynamo had reached the semi-finals of the competition, and they were only narrowly edged out over two legs by Bayern Munich as their European quest came to an end. Dynamo Kviv vs Real Madrid (3-1 on aggregate) 3 March 1999 Real Madrid 1-1 Dynamo Kyiv Predrag Mijatovic (66') Andriy Shevchenko (54') 17 March 1999 Dynamo Kyiv 2-0 Real Madrid Andriy Shevchenko (62', 79') N/A Twenty years after they were left stunned in the Ukrainian capital, Real Madrid were on the receiving end of an even more shocking defeat in the Champions League knockout phase. Having won the previous three editions of the tournament, Los Blancos expected to make easy work of an side, who hadn't won a knockout match in the competition in 22 years, and all looked to be going to plan when they won the first leg 2-1 in Amsterdam. However, 's side pulled off a truly remarkable comeback at the Bernabeu as early goals from Hakim Ziyech and David Neres saw them flip the score around in just 18 minutes before Dusan Tadic and Lasse Schone completed the
Job and saw Ajax emerge from Madrid with a memorable 4-1 victory. They proceeded to claim another major scalp in the quarter-finals as they beat before they were the victims of a miraculous comeback themselves - this time , in the semi-finals. Ajax vs Real Madrid (5-3) on aggregate) 13 February 2019 Ajax 1-2 Real Madrid Hakim Ziyech (75') Karim Benzema (60'), Marco Asensio (87') 5 March 2019 Real Madrid 1-4 Ajax Marco Asensio (70') Hakim Ziyech (7'), David Neres (18'), Dusan Tadic (62'), Lasse Schone (72') After lifting the trophy for the fifth time in 2015, failed to make it past the quarter-finals of the Champions League in the following two editions. It looked like being third time lucky when they were handed a relatively favourable draw with Roma in the last eight and obliterated the Italian side 4-1 in the first leg at the Nou Camp. However, just six days later, Eusebio Di Francesco's side took the Catalans back to the Stadio Olimpico and pulled off the most improbable of comebacks, with Kostas Manolas' glancing header eight minutes from time sending La Lupa through on away goals and prompting a spine-tingling monologue from commentator Peter Drury. The win saw Roma reach the semi-finals of the Champions League for only the second time in their history, and across two thrilling legs against , denying them a place in the final. 4 April 2018 Barcelona 4-1 Roma Daniele De Rossi (38' og), Kostas Manolas (55' og), Gerard Pique (59'), Luis Suarez (87') Edin Dzeko (80') 10 April 2018 Roma 3-0 Barcelona Edin Dzeko (6'), Daniele De Rossi (58' pen), Kostas Manolas (82') N/A In 2016/17, were still a work in progress in 's first season in charge, but were nonetheless expected to make easy work of a Monaco side 47 places below them in the coefficient rankings when the two teams were drawn to face each other in the Champions League round of 16. However, the French side weren't to be taken lightly and possessed numerous players who would soon be snapped up by Europe's elite, including a 19-year-old enjoying his breakout season. After the Citizens had edged a thrilling first leg in Manchester by a score of 5-3, they were stunned in the return leg in southern
France as Mbappe, Fabinho and Tiemoue Bakayoko all got their names on the score-sheet to send their side through on away goals. In the year Monaco pipped to the Ligue 1 title, they also reached the semi-finals of the Champions League for only the fourth time ever, after in the quarter-finals. Monaco vs Manchester City (6-6 on aggregate) 21 February 2017 Manchester City 5-3 Monaco Raheem Sterling (26'), Sergio Aguero (58', 71'), John Stones (77'), Leroy Sane (82') Radamel Falcao (32', 61'), Kylian Mbappe (40') 15 March 2017 Monaco 3-1 Manchester City Kylian Mbappe (8'), Fabinho (29'), Tiemoue Bakayoko (77') Leroy Sane (71') Undoubtedly the greatest shock in Champions League knockout football took place in 2012 as APOEL pulled off the unlikeliest of victories over Lyon in the round of 16. The Cypriot side had only qualified for the group stage of the competition once before the 2011/12 campaign kicked off, but were able to beat both Porto and Zenit and top Group G, setting up a round of 16 tie with French giants Lyon. Les Gones edged the first leg at home, winning 1-0 before APOEL repeated the scoreline back in Cyprus and took the match to a penalty shoot-out which they managed to win, after they had scored all their spot-kicks and goalkeeper Dionysis Chiotis had denied both Alexandre Lacazette and Michel Bastos from 12 yards out. They remain the only Cypriot side to ever reach the quarter-finals of the competition, although they ended up getting against Real Madrid. APOEL vs Lyon (1-1 on aggregate) (APOEL won 4-3 on penalties) 14 February 2012 Lyon 1-0 APOEL Alexandre Lacazette (58') N/A 7 March 2012 APOEL 1-0 Lyon Gustavo Manduca (9') N/A