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Following a pulsating penalty decider in Wednesday's semi-final clash, Goal.com looks at the most dramatic shoot-outs in Europe's glamour club competition

ANALYSIS
By KS Leong

It's not very often that the Champions League knockout phase outside of the final requires a penalty shoot-out to separate two evenly balanced rivals. But evenly balanced was exactly what Bayern Munich and Real Madrid were in their semi-final tie this season.

The fixture had been a topsy-turvy affair from the first leg, with the Bavarians netting a last-minute winner on home soil. The Spaniards completely turned the tie on its head just 15 minutes into the return clash at the Santiago Bernabeu, but Arjen Robben's spot-kick on 27 minutes ensured the contest would head into extra time, and eventually penalties where the drama continued.

Love them or hate them, fair or unfair, penalties are a lottery, a cruel game of chance to decide what is otherwise a battle of skill, flair, and tactical masterstrokes. But that is what makes them such a nail-biter.

Below, Goal.com looks at the five most dramatic penalty shoot-outs in the Champions League era.

BAYERN MUNICH 5-4 VALENCIA (1-1 a.e.t.)
2001 Champions League final


Paulo Sergio
 
Salihamidzic
Zickler
 Anderson 
Effenberg
Lizarazu
 Linke

Valencia CF

Mendieta
Carew
Zahovic
Carboni
Baraja
Kily
Pellegrino

Germans very rarely crumble when it comes to penalties, and that was the case in the 2001 final in San Siro. Much like Wednesday evening's semi-final between Madrid and Bayern, it was a game dominated by the dreaded white spot 12 yards out. Gaizka Mendieta converted a penalty just two minutes into the final, but Stefan Effenberg restored parity from the spot just after the interval, and that was how it stayed after 120 minutes of football.

The Bavarians went first in the shoot-out but Paulo Sergio blazed over the bar. Hasan Salihamidzic scored in between Mendieta and John Carew's successful conversions to give the Spaniards a 2-1 lead. Zlatko Zahovic then saw his attempt saved by Oliver Kahn after Alexander Zickler had netted. Patrick Anderson and Amedeo Carboni then missed for both teams in succession as they headed into the fifth kick levelled at 2-2. Effenberg, Ruben Baraja, Bixente Lizarazu and Kily Gonzalez all found the net as the pressure began to escalate in sudden death in the shoot-out. Thomas Linke didn't succumb to the nerves, but Mauricio Pellegrino did as Kahn saved his penalty and Bayern went on to lift their fourth European Cup 5-4 on penalties.

JUVENTUS 2-3 AC MILAN (0-0 a.e.t.)
2003 Champions League final


Trezeguet
 
Birindelli
Zalayeta
Montero
Del Piero

Serginho
Seedorf
Kaladze
Nesta
Shevchenko

The first all-Italian Champions League final produced a somewhat stereotypical 0-0 stalemate after 120 minutes at Old Trafford. The penalty shoot-out, however, was dominated by the goalkeepers as Dida and Gianluigi Buffon saved all the unsuccessful attempts.

David Trezeguet was the first to step up but his tame effort to his right was comfortably kept out by Milan's Brazilian shot-stopper. Serginho converted for the Rossoneri, before Alessandro Birindelli levelled proceedings. Clarence Seedorf then saw his kick palmed away by Buffon, but Dida responded with a block with his knees on Marcelo Zalayeta's effort. The two custodians continued to trade spectacular saves as Kakha Kaladze and Paolo Montero were next to be frustrated. With only two of seven penalties converted, Alessandro Nesta held his nerve to put Milan back in the lead 2-1 with four kicks apiece. Alessandro Del Piero netted his side's fifth to keep the Old Lady alive, until Andriy Shevchenko shot the Rossoneri to glory by converting the final penalty.

AC MILAN 2-3 LIVERPOOL (3-3 a.e.t.)
2005 Champions League final

Serginho
 
Pirlo
Tomasson
 Kaka
Shevchenko

Liverpool

Hamann
Cisse
Riise
Smicer
 

Milan didn't quite enjoy the same fortune from 12 yards two years later in Istanbul in what has been widely regarded as the most spectacular comeback in a European Cup final. The Italians cruised to a 3-0 lead at half-time against Liverpool, with the Reds camp claiming afterwards that their opponents had kicked off celebrations in the dressing room during the interval. Rafa Benitez's men duly rallied after the restart and drew levelled within 15 second-half minutes, and Milan were on the backfoot since, even in the shoot-out.

The Rossoneri went first this time but Serginho, who converted his side's opening kick two years ago, blazed over the bar after Jerzy Dudek's best Bruce Grobbelar imitation distracted the Brazilian. Dietmar Hamann made no mistakes to put Liverpool ahead, and when Djibril Cisse converted his effort after Andrea Pirlo was denied by Dudek, the Merseysiders looked in cruise control. Jon Dahl Tomasson eventually got Milan on the board but after Dida saved John Arne Riise's attempt, it was suddenly game on again. Kaka dispatched his penalty to make it 2-2, but Vladimir Smicer didn't buckle under pressure as he restored Liverpool's advantage. As fate would have it Shevchenko, the hero in 2003, became the villain in 2005 when his kick down the middle was fisted away by Dudek's trailing left arm. The Reds' astonishing comeback was complete as they triumphed 3-2 on penalties in one of the very rare occasions where regulation time eclipsed the suspense of the shoot-out.

MANCHESTER UNITED 6-5 CHELSEA (1-1 a.e.t.)
2008 Champions League final

Man Utd.

Tevez
Carrick
Ronaldo
 Hargreaves
Nani
Anderson
Giggs

Chelsea FC

Ballack
Belleti
Lampard
A. Cole
Terry
Kalou
Anelka

Five years after an all-Italian final came an all-English decider. And once again, it had to be settled by the lottery of the spot-kick after Manchester United and Chelsea were locked at 1-1 after extra time in Moscow.

The first four penalties went smoothly as Carlos Tevez, Michael Ballack, Michael Carrick and Juliano Belletti all rippled the back of the net. But it was the usually reliable Cristiano Ronaldo who was first to miss when Petr Cech guessed the right way despite the Portuguese's stuttering run-up. Frank Lampard put the Blues in charge when he converted, and after Owen Hargreaves, Ashley Cole and Nani all held up their end of the bargain, it was down to John Terry in the final penalty. But the captain infamously slipped just as he pulled the trigger and sent his shot against the post. United were gifted a lifeline as the shoot-out went into sudden death. Anderson scored and so did Salomon Kalou to make it 5-5; Ryan Giggs made it six to the Red Devils to shift all the pressure on to Nicolas Anelka. Edwin van der Sar played his part to jangle the Frenchman's nerves further when he pointed to his left. It worked as the Dutch keeper dived to his right to make the championship-winning save.

REAL MADRID 1-3 BAYERN MUNICH (3-3 agg.)
2012 Champions League semi-final second leg

Real Madrid CF

Ronaldo
 
Kaka
Alonso
 Ramos
 

Alaba
Gomez
Kroos
Lahm
Schweinsteiger

Not for the first time, Spanish hearts were broken by a German side in a Champions League shoot-out. And it wasn't even a final. Madrid looked to have successfully overturned Bayern's 2-1 semi-final first-leg advantage when a Cristiano Ronaldo double gave them a 2-0 lead inside 15 minutes. But Jose Mourinho's men failed to kill off the game and allowed Arjen Robben to force penalties after both sides settled for a 3-3 aggregate score after extra time.

In the shoot-out, it looked like it would be game over after three kicks when Real fluffed both their opening efforts, but Iker Casillas nearly inspired a comeback. Ronaldo, who had dispatched 25 successful penalties on the trot, showed his weakness in shoot-outs as for the second time following his 2008 miss in Moscow, he failed to convert when his weak effort was scooped up by Manuel Neuer. Kaka saw his near-identical kick to Ronaldo's kept out as David Alaba and Mario Gomez tucked away theirs to give Bayern a 2-0 lead on penalties. However, Xabi Alonso began the revival when he sent his effort straight down the middle and in between his conversion Casillas kept the contest alive when he saved from Toni Kroos and Philipp Lahm. Real were then presented with a chance to square it up 2-2, but Sergio Ramos smashed his attempt into the stands as the momentum swayed back to the Germans. Bastian Schweinsteiger held his nerve to bury the crucial fifth kick as Bayern emerged 3-1 winners on penalties to ensure a home final against Chelsea on May 19.

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