#6 The eye-gouging incident
After going on to win the Champions League with Inter, Mourinho moved to Real Madrid, and to no one’s surprise, his most controversial moment came when his side faced Barcelona. There was no love lost between Mourinho and then-Barca manager Pep Guardiola, with a lot of comments made in the press regarding the pair’s relationship.
In a Spanish Super Cup tie in 2011, a touchline brawl broke out after a wild tackle by Marcelo on Cesc Fabregas, with both benches getting involved. In perhaps Mourinho’s darkest hour as a football manager, he walked over to the Barcelona bench and poked his finger into the eye of coach Tito Vilanova. The incident made him the villain in the Spanish press, and perhaps remains his most embarrassing moment as a manager.