2012 against Bayern Munich
This was by far the most painful loss for a Real Madrid fan in recent history. After losing the first leg against Bayern at the Allianz Arena 2-1, Madrid fans were hopeful because of the away goal that the club scored.
And the second leg started off in the deadliest of fashions. Within 14 minutes, Real Madrid were leading 2-0 thanks to a Cristiano Ronaldo brace. Up until that point, the Blancos were playing relentlessly and Bayern knew not what to do.
However, Mourinho decided to take the steam off and play cautiously, a move that ultimately became Madrid’s downfall in that game.
Arjen Robben scored from the spot to make it 2-1 in the 27th minute and from then on it was something of a drab game that went to the extra-time and then shoot-outs. And it was a heartbreak for Madridistas. Mourinho sunk his knees in the ground, hoping that God would recognise his submission, but it wasn’t to be.
In the end, Bayern Munich won the penalty shoot-out 3-1.
First leg score: Bayern Munich 2-1 Real Madrid
Aggregate score: Bayern Munich 3-3 Real Madrid (Bayern won 3-1 via penalty shoot-out)