Chelsea 1-1 (4-3 on penalties) Bayern Munich (final, 2011/12)
Heading in to the 2012 Champions League final, Bayern Munich were the overwhelming favourites. The Bavarian giants were playing at home and Chelsea had barely survived with enough first team regulars after a bruising semi-final win over Barcelona.
But in the final the Blues kept doing what they did to eliminate Barcelona: put numbers behind the ball and do not allow Bayern Munich to play their game. The stoic defending seemed to unravel as they conceded an 83rd minute goal from Thomas Muller, but Didier Drogba scored a late equaliser to put the game into extra time. Incredibly, Chelsea triumphed in the penalty shootout to become unlikely champions.
Liverpool 3-3 (3-2 on penalties) AC Milan (final, 2004/05)
Not many gave the Reds much of a chance against Carlo Ancelotti’s AC Milan. The Rossoneri at the time were consistently performing well in European football’s elite competition and were expected to see out Liverpool, who had badly struggled in the league that season.
And the match, at least until half time, went according to the script as AC Milan raced to a 3-0 lead with an opening goal from the legendary Paolo Maldini and a brace from Hernan Crespo. But the Reds mounted a spirited comeback in the second half as they scored three goals in “six minutes of madness”. The match went to extra time and then a penalty shootout, where the Reds prevailed 3-2.
Dynamo Kyiv vs. Real Madrid (quarter-final, 1998/99)
In what was the last season for Andriy Shevchenko at Dynamo Kyiv before he signed for AC Milan, the legendary striker took the club to a level where they had never been before.
He scored the opening goal in a 1-1 draw against Real Madrid at the Santiago Bernabeu before scoring both the goals in the return fixture at home to eliminate Los Blancos from the competition and take his team to their first ever semi-final.
Porto 3-2 Manchester United (round of 16, 2003/04)
This was the season that helped Jose Mourinho earn renown the world over, and if it is to be pointed out then this was the match which truly made him and his Porto believe that they could, perhaps, go all the way. And so they did.
Porto had won the first leg at home 2-1, but their advantage disappeared when Paul Scholes scored in the second leg. However, Costinha scored to see his team through and sparked a crazy celebratory run along the touchline from Mourinho.
Deportivo La Coruna 5-4 AC Milan (quarter-final, 2003/04)
After the first leg at the San Siro that went 4-1 in favour of AC Milan, the second leg appeared to be a mere formality as Ancelotti’s men eyed a spot in the semi-final.
But they were completely blitzed away at the Raizor as Depor took a 3-0 lead into half time. A second half strike from Fran made the impossible possible as AC Milan went out of the tournament in the most unexpected fashion.