#3) Jose Mourinho: Real Madrid 0 – 5 Barcelona
Manchester United fans mocking Guardiola after City’s loss to Everton might want to skip this one as the current United boss’ biggest defeat came against arch rival Guardiola during his first season in charge of Real Madrid. Having been a treble winner at Inter Milan and undefeated in charge of Madrid, Mourinho’s first Clasico would be his worst with a David Villa brace – along with goals from Xavi, Pedro and Jeffren – sending his side a shock they never recovered from in the title race.
Over the coming years, Mourinho has adapted better to taking on Guardiola but his spell at Manchester United brought him face to face with Antonio Conte – in charge of Mourinho’s former club Chelsea – who inflicted a 4-0 defeat that’s the second worst of his career.
