9. Rafael's Red Card vs Bayern Munich
Matthias Scharader/AP/Press Association ImagesIn April 2010, Manchester United were well on course to reach a third consecutive Champions League final, and might have done so had it not been for a moment of madness from Rafael. United had lost the first leg of their quarter-final to Bayern Munich 2-1 but had scored a vital away goal in the German capital to give them the advantage. And things got better still at Old Trafford in the second leg when goals from Darren Gibson and Nani gave the Red Devils an astonishing 3-1 halftime lead. The Red Devils looked like dead certs to reach the semi-finals, up 4-3 on aggregate, but the tie was turned on its head when Rafael picked up a second yellow card for needlessly hauling down Franck Ribery. The tide was turned against 10-man United and Bayern went on to score another goal through Arjen Robben in the 74th minute to settle the tie-4-4 on aggregate, and reach the semis on the away goal rule. It was heartbreak for the Reds, as a team managed by, guess who, Louis van Gaal went through at their expense.