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The five greatest Champions League last 16 ties ever, from Porto vs Manchester United to Chelsea vs Barcelona
Ahead of the draw for this season's first knockout round in Europe's top club tournament, Goal.com looks back at the most memorable encounters from this stage of the competition
15 Dec 2011 08:04:00
By Graham Lister
For European Cup traditionalists and those who relish the high stakes of sudden-death football, the knockout stages of the Champions League are what it's all about, and Friday's draw for the Round of 16 is once again likely to throw up some potentially epic contests.
Uefa only introduced the knockout Round of 16 in 2003-04. Prior to that there was either an initial round of 32 to determine the composition of the group stage, then quarter-finals, semis and final; or a second group stage leading straight into the quarter-finals.
But in the eight seasons it's been contested, the Round of 16 has generated some classic encounters. Goal.com recalls the best of them...
Jose Mourinho memorably impinged upon the consciousness of England’s football-following public, scampering up the Old Trafford touchline in uninhibited jubilation as his team dumped Sir Alex Ferguson’s Premier League champions out of Europe in dramatic fashion.
Porto may have been Uefa Cup holders and Portugal’s double champions, but they were underdogs against United. After all, they’d finished three points behind Real Madrid in Group F, while United had won Group E with three to spare.
When Quinton Fortune fired the visitors ahead after 14 minutes at the Estadio do Dragao, United seemed on course for the quarter-finals. But with a volley and a header, Benni McCarthy scored spectacularly in each half; and when captain Roy Keane was sent off late on things suddenly looked complicated for the Red Devils.
Nevertheless, with Keane banned, United went ahead in Manchester when John O’Shea’s cross was headed in at the near post by Paul Scholes. Sir Alex’s side now led the tie on away goals. Scholes had an effort disallowed for offside, but Porto refused to buckle, and in the closing stages put the home defence under sustained pressure. It finally told when, with 30 seconds remaining, Tim Howard could only parry McCarthy’s free kick, leaving Costinha – suspended for the first leg – to plant the rebound into the net.
Mourinho’s Inter had defeated Bayern 2-0 to become European champions the previous May, defending their crown under Leonardo they met the Bavarians in the round of 16 with Louis van Gaal seeking to avenge that final defeat. It certainly started well for Bayern. Both sides had created but failed to convert a host of chances in a stirring contest at the San Siro before the Germans clinched a priceless away win in the final minute. Julio Cesar spilled Arjen Robben’s shot, and Mario Gomez buried the loose ball.
Bayern's 1-0 first-leg lead lasted just four minutes at the Allianz Arena though, Samuel Eto'o making the most of Goran Pandev’s astute pass. Yet on 21 minutes Gomez equalised with a piece of virtuosity when Julio Cesar again failed to hold a Robben shot. And 10 minutes later Bayern led 2-1 on the night and 3-1 on aggregate, Thomas Muller finding the bottom corner when the ball came to him off Thiago Motta.
Andrea Rannochia had to clear via a post and Julio Cesar saved a goal-bound Gomez volley before Wesley Sneijder beat Thomas Kraft with a low shot to haul Inter back into contention. Then two minutes from time Eto’o deftly laid the ball off for Pandev to finish coolly and send Inter through on the away goals rule.
Werder Bremen, third in the Bundesliga in 2004-05, had to beat Basel in a qualifier to take their place in the group stage, where they finished second, a distant nine points behind Barcelona. In contrast, Serie A champions Juventus comfortably won their group. Yet the German side earned a potentially crucial advantage to take to Turin for the second leg.
A dramatic encounter saw four goals scored in the final 20 minutes after Christian Schulz had put Bremen ahead in the first-half. Pavel Nedved and David Trezeguet struck late to turn things Juve’s way, only for resilient Bremen to hit back. Tim Borowski equalised three minutes from time before Johan Micoud headed home from a corner. The final whistle sounded seconds later, leaving the German fans ecstatic.
The return was equally compelling, especially after Weserstadion hero Micoud extended Bremen’s lead on 13 minutes. When Borowski almost added another, the Old Lady was apparently on her knees. But Fabio Capello masterminded a gutsy fight-back. He sent on Alessandro Del Piero and Adrian Mutu, and soon Juve were level, Nedved and Trezeguet combining sweetly for the Frenchman to beat Tim Wiese. The keeper then defied Juve until the 88th minute, when he gifted the ball to Emerson under little pressure and the midfielder swept it in to take the Bianconeri through on away goals.
German champions and Group B winners Bayern met Real Madrid, runners-up to Lyon in Group E, who went into a vibrant first leg at the Bernabeu having scored just twice in their previous four Primera Division games. Madrid coach Fabio Capello gave Champions League debuts to Argentine pair Gonzalo Higuain and Fernando Gago, but it was Raul who put them ahead on 10 minutes when he latched onto Ruud van Nistelrooy’s incisive through-ball.
Bayern equalised with their first meaningful attack, Lucio heading home Willy Sagnol’s free kick at the far post. Five minutes later Real were back in front, Raul applying the finish to Ivan Helguera’s teasing header. And before half-time Helguera flicked on a David Beckham free kick for the unmarked Van Nistelrooy to beat Oliver Kahn. Claudio Pizarro headed against the post and was then thwarted by Iker Casillas before Mark van Bommel scored Bayern’s second in the 88th minute to set up an enthralling return.
It began explosively, Roy Makaay netting inside 11 seconds (the fastest Champions League goal in history) to wipe out Madrid’s advantage. Lucio doubled Bayern's lead after the break, and although Van Nistelrooy made it 2-1 from the spot after Mahamadou Diarra and Van Bommel had been sent off, Bayern progressed, later losing to eventual champions AC Milan.
The 50th season of Europe’s premier club tournament pitted Frank Rijkaard’s Barcelona against Mourinho’s Chelsea in two passionate and pulsating encounters. At Camp Nou Barca attacked with verve but were caught out on 33 minutes pressing high up the pitch. Chelsea broke through Frank Lampard, Damien Duff and Joe Cole, whose shot Juliano Belletti could only deflect high into his own net. Didier Drogba should have added another but was then dismissed for a second bookable offence.
His departure infused Barca with confidence, and substitute Maxi Lopez, a Champions League debutant, turned William Gallas and smashed home a stunner on 67 minutes. Six minutes later Samuel Eto'o converted Lopez’s cross-shot, and Chelsea had to defend desperately to hold the score at 2-1.
A sensational Stamford Bridge second leg saw the Blues race into an commanding 3-0 lead within the opening 19 minutes. Goals from Eidur Gudjohnsen, Lampard and Duff had Barca reeling. But the Catalans recovered, and when Belletti’s cross struck Paulo Ferreira’s arm, Ronaldinho beat Petr Cech from the spot. The reigning world player of the year then scored a wondrous second with the outside of his boot.
Cole hit the post, Cech saved superbly from Carles Puyol and turned an Andres Iniesta effort against an upright as the game flowed exhilaratingly from end to end. It was finally settled 14 minutes from time when Blues’ skipper John Terry rose to head a Duff corner into the net.
Uefa only introduced the knockout Round of 16 in 2003-04. Prior to that there was either an initial round of 32 to determine the composition of the group stage, then quarter-finals, semis and final; or a second group stage leading straight into the quarter-finals.
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But in the eight seasons it's been contested, the Round of 16 has generated some classic encounters. Goal.com recalls the best of them...
| 5. PORTO 3-2 MANCHESTER UNITED (2-1; 1-1) 2003-04 |
Jose Mourinho memorably impinged upon the consciousness of England’s football-following public, scampering up the Old Trafford touchline in uninhibited jubilation as his team dumped Sir Alex Ferguson’s Premier League champions out of Europe in dramatic fashion.
Porto may have been Uefa Cup holders and Portugal’s double champions, but they were underdogs against United. After all, they’d finished three points behind Real Madrid in Group F, while United had won Group E with three to spare.
When Quinton Fortune fired the visitors ahead after 14 minutes at the Estadio do Dragao, United seemed on course for the quarter-finals. But with a volley and a header, Benni McCarthy scored spectacularly in each half; and when captain Roy Keane was sent off late on things suddenly looked complicated for the Red Devils.
Nevertheless, with Keane banned, United went ahead in Manchester when John O’Shea’s cross was headed in at the near post by Paul Scholes. Sir Alex’s side now led the tie on away goals. Scholes had an effort disallowed for offside, but Porto refused to buckle, and in the closing stages put the home defence under sustained pressure. It finally told when, with 30 seconds remaining, Tim Howard could only parry McCarthy’s free kick, leaving Costinha – suspended for the first leg – to plant the rebound into the net.
| 4. INTER 3-3 BAYERN MUNICH (0-1; 3-2) 2010-11 (Inter won on away goals) |
Mourinho’s Inter had defeated Bayern 2-0 to become European champions the previous May, defending their crown under Leonardo they met the Bavarians in the round of 16 with Louis van Gaal seeking to avenge that final defeat. It certainly started well for Bayern. Both sides had created but failed to convert a host of chances in a stirring contest at the San Siro before the Germans clinched a priceless away win in the final minute. Julio Cesar spilled Arjen Robben’s shot, and Mario Gomez buried the loose ball.
Bayern's 1-0 first-leg lead lasted just four minutes at the Allianz Arena though, Samuel Eto'o making the most of Goran Pandev’s astute pass. Yet on 21 minutes Gomez equalised with a piece of virtuosity when Julio Cesar again failed to hold a Robben shot. And 10 minutes later Bayern led 2-1 on the night and 3-1 on aggregate, Thomas Muller finding the bottom corner when the ball came to him off Thiago Motta.
Andrea Rannochia had to clear via a post and Julio Cesar saved a goal-bound Gomez volley before Wesley Sneijder beat Thomas Kraft with a low shot to haul Inter back into contention. Then two minutes from time Eto’o deftly laid the ball off for Pandev to finish coolly and send Inter through on the away goals rule.
| 3. WERDER BREMEN 4-4 JUVENTUS (3-2; 1-2) 2005-06 (Juve won on away goals) |
Werder Bremen, third in the Bundesliga in 2004-05, had to beat Basel in a qualifier to take their place in the group stage, where they finished second, a distant nine points behind Barcelona. In contrast, Serie A champions Juventus comfortably won their group. Yet the German side earned a potentially crucial advantage to take to Turin for the second leg.
A dramatic encounter saw four goals scored in the final 20 minutes after Christian Schulz had put Bremen ahead in the first-half. Pavel Nedved and David Trezeguet struck late to turn things Juve’s way, only for resilient Bremen to hit back. Tim Borowski equalised three minutes from time before Johan Micoud headed home from a corner. The final whistle sounded seconds later, leaving the German fans ecstatic.
The return was equally compelling, especially after Weserstadion hero Micoud extended Bremen’s lead on 13 minutes. When Borowski almost added another, the Old Lady was apparently on her knees. But Fabio Capello masterminded a gutsy fight-back. He sent on Alessandro Del Piero and Adrian Mutu, and soon Juve were level, Nedved and Trezeguet combining sweetly for the Frenchman to beat Tim Wiese. The keeper then defied Juve until the 88th minute, when he gifted the ball to Emerson under little pressure and the midfielder swept it in to take the Bianconeri through on away goals.
| 2. REAL MADRID 4-4 BAYERN MUNICH (3-2; 1-2) 2006-07 (Bayern won on away goals) |
German champions and Group B winners Bayern met Real Madrid, runners-up to Lyon in Group E, who went into a vibrant first leg at the Bernabeu having scored just twice in their previous four Primera Division games. Madrid coach Fabio Capello gave Champions League debuts to Argentine pair Gonzalo Higuain and Fernando Gago, but it was Raul who put them ahead on 10 minutes when he latched onto Ruud van Nistelrooy’s incisive through-ball.
Bayern equalised with their first meaningful attack, Lucio heading home Willy Sagnol’s free kick at the far post. Five minutes later Real were back in front, Raul applying the finish to Ivan Helguera’s teasing header. And before half-time Helguera flicked on a David Beckham free kick for the unmarked Van Nistelrooy to beat Oliver Kahn. Claudio Pizarro headed against the post and was then thwarted by Iker Casillas before Mark van Bommel scored Bayern’s second in the 88th minute to set up an enthralling return.
It began explosively, Roy Makaay netting inside 11 seconds (the fastest Champions League goal in history) to wipe out Madrid’s advantage. Lucio doubled Bayern's lead after the break, and although Van Nistelrooy made it 2-1 from the spot after Mahamadou Diarra and Van Bommel had been sent off, Bayern progressed, later losing to eventual champions AC Milan.
| 1. CHELSEA 5-4 BARCELONA (1-2; 4-2) 2004-05 |
The 50th season of Europe’s premier club tournament pitted Frank Rijkaard’s Barcelona against Mourinho’s Chelsea in two passionate and pulsating encounters. At Camp Nou Barca attacked with verve but were caught out on 33 minutes pressing high up the pitch. Chelsea broke through Frank Lampard, Damien Duff and Joe Cole, whose shot Juliano Belletti could only deflect high into his own net. Didier Drogba should have added another but was then dismissed for a second bookable offence.
His departure infused Barca with confidence, and substitute Maxi Lopez, a Champions League debutant, turned William Gallas and smashed home a stunner on 67 minutes. Six minutes later Samuel Eto'o converted Lopez’s cross-shot, and Chelsea had to defend desperately to hold the score at 2-1.
A sensational Stamford Bridge second leg saw the Blues race into an commanding 3-0 lead within the opening 19 minutes. Goals from Eidur Gudjohnsen, Lampard and Duff had Barca reeling. But the Catalans recovered, and when Belletti’s cross struck Paulo Ferreira’s arm, Ronaldinho beat Petr Cech from the spot. The reigning world player of the year then scored a wondrous second with the outside of his boot.
Cole hit the post, Cech saved superbly from Carles Puyol and turned an Andres Iniesta effort against an upright as the game flowed exhilaratingly from end to end. It was finally settled 14 minutes from time when Blues’ skipper John Terry rose to head a Duff corner into the net.
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