2005: AC Milan
Beaten by: Liverpool (on penalties, 3-3 AET)
Following season’s finish: Semi-finals
The Milan side of Kaka, Andrea Pirlo and Paolo Maldini only had to wait a couple years to get revenge for the ‘Miracle of Istanbul’, in which Liverpool came back from three goals down to win on penalties. The defeat was so traumatising Pirlo considered quitting football. “For some days I really thought it was over. I had no strength left,” he told Tuttosport a few years ago. They showed the mental strength to reach the semi-finals in the next season, however, losing narrowly to eventual winners Barcelona. The 2007 campaign produced a rematch with Liverpool in the final, which Milan won 2-1 thanks to two goals from Pippo Inzaghi.