1) Barcelona 5-0 Real Madrid
Perhaps what can only top such a humiliating defeat against a lesser side for Mourinho is the dismantling his expensively built Real Madrid side suffered at the hands of Pep Guardiola’s Barcelona in 2010.
Despite coming into his first Clasico on the crest of a wave, his side were on a seven-game win streak, Real were 2-0 down in 18 minutes and 4-0 down before the 60th.
Sergio Ramos capped off the horrific display with a late red card after striking Carles Puyol in the face.
Mourinho admitted after he was simply watching the clock run down in the second-half as he realised he could do nothing to stem the tide.
It still remains the biggest loss in the career of the ‘Special One’.
BONUS! Chelsea 1-2 Sunderland
Bottom of the table Sunderland seemed the unlikeliest side possible to end Jose Mourinho’s impregnable record as Chelsea boss of playing 78 Premier League games at Stamford Bridge without defeat, his entire career as Blues boss.
But Gus Poyet’s side did just that in a tumultuous day for the Londoners which saw goals from Connor Wickham and Fabio Borini.
Borini’s proved to be the most contentious for the Chelsea ranks with assistant boss Rui Faria having to be dragged away by coaches, stewards and even Mourinho after trying to confront referee Mike Dean.