8 Champions League matches that left an open wound for the defeated

Ask any manager for the matches that made them and you may be surprised.

Because more often than not, the games that define your life in football are not the ones in which you got a positive result. It's the defeats that leave scars and push you onto bigger and better things. 

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That's certainly true of these eight Champions League nights. Allow us to present a history of managers not eating, not forgetting and sometimes wandering the streets of Athens in search of reflection. 

1. Liverpool’s Greek Tragedy

Liverpool were a more cohesive unit than the 2005 version but couldn’t make pressure count as Milan got their revenge for Istanbul with a Filippo Inzaghi brace. 

Peter Crouch, who was controversially left out of the starting XI, said: “Some of the lads who were involved that night have gone 11 years without watching the highlights and I can understand why. It was a game we should have won, a wonderful opportunity missed.” 

Steven Gerrard claimed there wasn’t enough pace in the line-up to test out Milan, who fielded the oldest starting XI in Champions League final history. In his Champions League Dreams book, Rafa Benitez recounts wandering the streets of Athens in the early hours wondering where it all went wrong...

2. Pochettino's house arrest

Mauricio Pochettino never really got over Tottenham’s 2019 final defeat to Liverpool in Madrid. The epic victories over Manchester City and Ajax counted for nothing as Spurs knocked and knocked at the red brick wall but were undone by goals at the start and finish of the match. 

“I spent 10 days in my house, and I didn't want to go out,” The Argentinian later recalled. The emptiness was still apparent when he returned for the new season, especially after a 7-2 humbling by Munich in the same competition. Seven weeks later he was sacked with Spurs 14th in the Premier League.

3. Pep gets pipped by Poch

Pep Guardiola’s Champions League misery over the last decade is well-documented. What really shattered his world was going out to Tottenham in that epic Etihad 2019 quarter-final. 

Fate looked like it was finally landing in Pep’s court when Raheem Sterling scored  in injury-time to make it 5-3 and 5-4 on aggregate after a ping-pong of first-half goals.  When the cruel dagger of VAR deemed Aguero offside after a minute of delirium, the manager slumped to his knees in slow motion with his head in his hands.

“More than 55,000 people went from joy and happiness and within one second everyone was devastated,” Guardiola said. “There is not an activity in this world you can put in these limits. Always it will remain in our hearts.”

4. Wenger's Parisian nightmare

2006 looked like the year Arsenal were finally going to break their Champions League hoodoo. 

The Gunners saw off Juve, Madrid and Villarreal in the knockout phase. Despite Jens Lehmann’s red card after 18 minutes, they were even leading Barca at the Parc des Princes with 14 minutes to go until Samuel Eto’o and substitute Juliano Belletti ripped it all away.

“It remains a regret – a big regret, especially when we were so close. My biggest regret is that we had to play with 10 men,” Arsene Wenger told FourFourTwo. “You go into the final, and you haven’t conceded a goal against Real Madrid with Zidane, Beckham and Ronaldo, or Juventus with Ibrahimovic and Trezeguet. It was hard to swallow and it still is today – but it’s part of life.”

5. Fergie-time fuels Munich misery

Bayern Munich were in a winning position for 84 minutes of the match, only to be denied by injury-time goals from Teddy Sheringham and the baby-faced assassin Ole Gunnar Solskjaer. 

The enduring image of agony is Bayern’s Sami Kuffour crumpling to the floor and banging the ground in total devastation. The defender said: “It still gives me pain. I need to let it go but I'm still holding it in my heart. It's very difficult and I don't want to watch it.  When I go to any airport in the world people always recognise me because of that. They say, 'Oh Sammy remember Manchester United against Bayern Munich' – no.”

Even the great Ottmar Hitzfeld knew there would be difficult days ahead. ”It could take days or even weeks to recover from this,” he claimed. Fortunately for Munich,  they made no such mistake against Valencia two years later.

6. Drogba flattens Bayern’s post-match party fizz

Munich was all set up for one hell of a post-match banquet. Playing on their home ground against a depleted Chelsea, there was only going to be one winner. Surely? 

Bayern battered the Blues with 35 shots and yet only broke the deadlock with Thomas Muller’s header seven minutes before the end of 90. Didier Drogba equalised with just two minutes remaining and the rest is history. 

“I couldn't eat for two days straight after that, it hurt so much,”  Jerome Boateng admitted. Toni Kroos hit the tequila so hard at home that he called an emergency doctor. Arjen Robben, who missed a decisive extra-time penalty, didn’t fancy drowning his sorrows at all by the looks of it, as he was pictured looking deep in thought later.

The Dutchman cheered up massively a year later when he squeezed in a late winner against Jurgen Klopp’s Dortmund at Wembley. It all ends well, Arjen.

7. Fergie's Glasgow blow

Despite two Champions League trophies, Sir Alex Ferguson was haunted constantly by two semi-final defeats. 

In 1997, he called the loss to eventual winners Dortmund  “an earthquake of disappointment”. Even worse, Glasgow was booked for the climax of the 2002 version, but United were held 2-2 by a Michael Ballack-inspired Leverkusen at Old Trafford and could only draw the return 1-1 when away goals (remember them?) counted. 

Fergie blamed the bad vibes he felt in checking out the Glasgow hotels before reaching the final. Roy Keane was less superstitious: “We blew it. This club belongs in the European Cup final and it's a disaster and very disappointing.”

8. Malaga go mental over injury-time exit

It’s not just United that score twice in injury-time. Jurgen Klopp’s Dortmund pulled their 2013 quarter-final against Malaga out of the fire with goals from Marco Reus and Felipe Santana to secure a 3-2 win. It was cruel on the Spanish side who threatened to make an official UEFA complaint. 

“There was in effect no referee on the pitch in the last seven minutes of the match,” manager Manuel Pellegrini raged. “I don’t know if one should call it a pure atrocity.” 

Six years later the two met again in the Premier League, when Klopp’s Liverpool were stung by a 1-1 draw at West Ham in their title charge - and it was clear Pellegrini was still bitter. 

“He beat me against Malaga with a goal that was seven metres offside,” the Chilean seethed. “So he cannot complain about anything.”

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