Chelsea crashed out of the Champions League last night in the last-16 against Paris Saint Germain despite twice taking a lead at Stamford Bridge.
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The Special One is hardly looking that this morning with the many predictions at the start of the season of a year of untold success for the Blues looking a far-off pipe dream.
His and Chelsea’s European hopes are in tatters following this latest damaging defeat and it waits to be seen how this will affected their domestic campaign.
But how does the PSG loss rank with some of the other significant losses of Jose’s predominantly spotless career?
Atletico Madrid 2-1 Real Madrid
In the self-labelled “worst season of my life”, Madrid failed in their only chance for silverware in 2013 with a defeat to Atletico Madrid.
To make matters even worse, the venue chosen for the bout was the Bernabeu itself with the match finishing 2-1 thanks to a Joao Miranda header deep into extra time.
The match saw 14 yellow card, two reds and Mourinho sent to the stands whilst it was the first time since 1999 that Atleti had beaten their fiercest rivals.
Tottenham Hotspur 5-3 Chelsea
In only the second time in his career, a Mourinho managed side conceded five goals in a game which saw Chelsea lose ground in the Premier League title race.
Less than two months previous to the game, Chelsea had an ever assailing eight point lead over their nearest title rivals but the Spurs game proved to be the nadir of a particularly dour run of form that eventually let Manchester City back in the hunt.
For once though, Mourinho didn’t blame some kind of elaborate conspiracy seemingly accepting his side were simply bested on the day.
Borussia Dortmund 4-1 Real Madrid
The stage looked set for a Real/Barcelona final at Wembley but, in what could be seen as a metaphor for the respective popularity of their respective football leagues in recent seasons, both Spanish sides were destroyed by their German opponents.
Madrid’s European demise befell them at the Westfallstadion with an inspired performance from Robert Lewandowski tearing Los Blancos apart, scoring Dortmund’s four goals himself.
The result was likely Mourinho’s worst in 106 Champions League games.
2) Chelsea 2-4 Bradford City
It may go down as one of the most shocking FA Cup results of all time after Chelsea, then Premier League leaders and statistically the best side in English football surrendered a two goal lead, at home, to League One Bradford City.
Mourinho had said it would be a disgrace to lose to such a lower placed side in what could be perceived as underhand digs at the likes of Arsene Wenger for his 2012 defeat to the Bantems.
But his words certainly came back to haunt him with their oponents, ranked 49 places below the Blues, fighting back from such an improbable position despite Chelsea fielding the likes of Cesc Fabregas and Eden Hazard.
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.