2007: Liverpool
Beaten by: Milan (2-1)
Following season’s finish: Semi-finals
The drama of 2005 sometimes overshadows how generally solid Liverpool were in the Champions League under Benitez. Liverpool made the semi-finals the season after losing the grudge match against Milan, where they were eliminated by Chelsea, who repeated the trick the following campaign (2008/09) at the quarter-final stage. So began a miserable decade of European football. Liverpool failed to make it out of the groups in Benitez’s final season and did not return to the Champions League till 2014/15, where (again) they didn’t make the knockout stage. Two final appearances under Jurgen Klopp in recent seasons (one successful) have remedied this.