Bayern, Paris, Porto and Inter feature as UEFA.com picks out a classic UEFA Champions League last-16 tie from each of the last 20 seasons.
Article top media content
The 2023/24 UEFA Champions League is the 21st edition since the knockout round of 16 replaced the second group stage. UEFA.com picks out a classic tie from each of the past 20 seasons – all headline scores are aggregate.
Most round of 16 appearances by club (2022/23 included)
20 Real Madrid
This was just the start for eventual champions Porto. Two Benni McCarthy goals helped earn a 2-1 first-leg win in the first European match at their new Estádio do Dragão, and the Old Trafford return leg made José Mourinho a global star – his famous charge down the touchline being prompted by Costinha's 90th-minute strike, which came with Porto 1-0 down and heading out on away goals.
For sheer impudence and execution, Ronaldinho's second goal at Stamford Bridge remains hard to match. It was, however, a mere footnote in a thrilling tie. Unperturbed by a 2-1 loss and red card for Didier Drogba at the Camp Nou, Chelsea were 3-0 up within 19 minutes of the return game. Although Ronaldinho's double threatened to derail the west London club, a header by captain John Terry finally secured a notable victory.
David Trezeguet put Juve 2-1 ahead with eight minutes left of the first leg in Bremen, but had little time to celebrate, the hosts striking twice to emerge 3-2 winners. The Frenchman's effort ultimately settled the tie on away goals, though; Bremen took the lead at the Stadio Delle Alpi, but goals from Trezeguet and Emerson made it 4-4 on aggregate to ensure a tense yet satisfactory finish for Juve.
Two goals in four minutes – 1,500km and a fortnight apart – turned this contest. Madrid led 3-1 at home courtesy of Raúl González and Ruud van Nistelrooy, but Mark van Bommel's 88th-minute effort gave Bayern hope for the return, and Roy Makaay promptly levelled matters with the competition's fastest goal. Lúcio rubber-stamped victory, although Van Nistelrooy's late strike made for a nervy finale.
Most round of 16 appearances by player
36 Cristiano Ronaldo (Manchester United, Real Madrid, Juventus)
34 Lionel Messi (Barcelona, Paris)
27 Iker Casillas (Real Madrid, Porto)
26 Karim Benzema (Real Madrid)
25 Andrés Iniesta (Barcelona)
25 Sergio Ramos (Real Madrid)
Sevilla were twice ahead in this tie but still went out. Zico's Fenerbahçe had been pegged back twice in Istanbul before Semih Şentürk wrapped up a 3-2 win on the night. Sevilla then came roaring back at home, and were 11 minutes from victory until being taken to extra time. Neither team could find the knockout punch, Volkan Demirel eventually taking the plaudits with three shoot-out saves.
The biggest aggregate triumph in Champions League history, this was scarcely a contest from the moment Franck Ribéry fired Bayern in front just before half-time in Lisbon. A 5-0 victory ensued and, back in Germany, six different scorers enabled Bayern to equal the then record for biggest winning margin in a single knockout game.
United did not quite match their feat from three seasons prior of putting seven past Roma in one game, but this was another ruthless display from Sir Alex Ferguson's men. Two Wayne Rooney goals contributed to a 3-2 success at the San Siro which set the scene for a vintage Old Trafford performance. Rooney was again at the double as United's pace, power and purpose told.
Bayern keeper Thomas Kraft's heroics underpinned Mario Gomez's 90th-minute winner in Milan, though this repeat of the 2010 final was far from over. Samuel Eto'o swiftly drew holders Inter level in Bavaria, only for Bayern to go 3-1 up on aggregate inside 31 minutes. However, in a final twist, Wesley Sneijder and (two minutes from time) Goran Pandev struck to send the Nerazzurri through.
The first Cypriot side to reach the knockout phase, Ivan Jovanović's APOEL lost 1-0 in Lyon before forcing extra time in Nicosia courtesy of an early effort from Gustavo Manduca. The goalscorer's 115th-minute red card might have unsettled APOEL, but goalkeeper Dionisios Chiotis kept his cool as the hosts came out on top in the ensuing shoot-out.
Jupp Heynckes' men led 2-0 within 21 minutes of the north London opener, and ended up 3-1 victors on the night, but the second leg would be anything but a formality. Olivier Giroud gave the Gunners early encouragement and Laurent Koscielny's finish made for a frantic final few minutes – but Bayern hung on. They would be back in the English capital come May.
New boss David Moyes steered United through the group stage unbeaten, but his team went down 2-0 in the Piraeus first leg. The Greek champions had lost on all 11 previous visits to England, however, and Robin van Persie's 25th-minute penalty at Old Trafford had Olympiacos nerves jangling. The Dutchman made it 2-2 on the stroke of half-time, before curling in a free-kick early in the second period to complete the comeback.
Having drawn 1-1 in Paris, Chelsea may have felt their luck was in when Paris talisman Zlatan Ibrahimović was sent off on 31 minutes at Stamford Bridge. Gary Cahill put Mourinho's men ahead late on, yet David Luiz's even later leveller forced extra time. There, Eden Hazard's 96th-minute penalty restored Chelsea's advantage, only for Thiago Silva's header six minutes from time to reward a superlative Paris effort.
This was the first Champions League knockout tie to finish goalless after two legs plus 30 minutes of extra time. PSV had lost Gastón Pereiro to a red card early in the second half in Eindhoven, but clung on for a draw. Atlético then had twice as many shots in the return leg – 24 – but still it went to penalties, PSV's Luciano Narsingh striking the crossbar with the 15th kick of the shoot-out to allow Juanfran to win it.
Paris's 4-0 first-leg demolition of Barcelona inspired an even crazier result at the Camp Nou. It was 2-0 to Barça by the break, and Lionel Messi struck from the spot soon after half-time. However, Edinson Cavani's away goal should have finished it, but with two minutes of regulation time left, Neymar went into overdrive – his free-kick followed by a penalty and an assist for Sergi Roberto combined to win the tie five minutes into added time.
"The Lions of Wembley" was Corriere dello Sport's headline after Juve thwarted Spurs, who had rallied from 2-0 down to draw 2-2 in the first leg, Gonzalo Higuaín failing to complete a hat-trick when he blazed a penalty against the crossbar. Heung-Min Son put the hosts ahead in the first half of the return leg, but Higuaín and Paulo Dybala struck in quick succession after the interval to forge on to the last eight.
Marcus Rashford converted a 94th-minute penalty as United completed a historic comeback to snatch a place in the quarter-finals. No side had ever recovered from a 2-0 home defeat in the Champions League knockout stage, but Romelu Lukaku's goal inside two minutes at the Parc des Princes set the visitors on course for a famous triumph.
Atlético headed to Anfield with a 1-0 lead to protect, but this was no vintage Diego Simeone shutout. Georginio Wijnaldum levelled the aggregate scores and the Reds threw everything at the visitors as the game headed to extra time. Atlético looked down and out when Roberto Firmino put the hosts in front, but then came an extraordinary turnaround. Marcos Llorente offered hope which soon turned into a 3-2 aggregate lead thanks to his second; Álvaro Morata provided the 121st-minute gloss.
Ten-man Porto miraculously progressed despite a 3-2 second-leg defeat. Sérgio Oliveira did in fact sweep the visitors in front from the spot, but the tide turned in the space of 15 second-half minutes. Federico Chiesa fired Juventus level and headed in their second, with Porto reduced to ten men in between. And yet they held out for extra time, then delivered the decisive blow when Sérgio Oliveira's free-kick beat Wojciech Szczęsny. Adrien Rabiot nodded in two minutes later, but it wasn't enough.
When first-leg match winner Kylian Mbappé doubled the French side's aggregate lead at the Santiago Bernabéu, there appeared only one winner in this tie. Carlo Ancelotti's side had barely laid a glove on Paris until Karim Benzema forced an error in the 61st minute, and the striker grabbed two more in three frenetic minutes to turn the tide. Such comebacks proved to be a regular feature as Madrid went on the win the trophy again.
Joško Gvardiol's towering header earned the German side a 1-1 draw in the first leg but they ran into the unstoppable force of Erling Haaland in the return. The Norwegian striker's 22nd-minute penalty started an avalanche of goals – 35 minutes later he had an astonishing five to his name. Ilkay Gündoğan made it four amongst Haaland's glut and Kevin De Bruyne's brilliant effort capped a remarkable 7-0 success.