Jose Mourinho’s worst ever defeats – ranked

Jose Mourinho’s worst ever defeats – ranked

Even one of the greatest manager’s of all-time isn’t exempt from embarrassing defeats during his career.

The latest on the list of the great Jose Mourinho came in the Europa League, as his Tottenham side blew a 2-0 first leg lead to be dumped out of the competition at the last 16 stage by Dinamo Zagreb.

It was one of the worst defeats of his career, but was it the worst? 90min takes a look at how bad things have been at various points of the ‘Special One”s career…

Sergio AgueroSergio Aguero
Chelsea were defending champions but were handily beaten | Alex Livesey/Getty Images

After Mourinho returned to the Premier League and won the title with Chelsea again, they began to crumble in his third season (shock).

Goals from Sergio Aguero, Vincent Kompany and Fernandinho meant Chelsea opened their season without a win in the first two games for the first time since 1998.

They had to wait until the 70th minute for their first shot on target in the game, and Mourinho ended up getting sacked later that season.

Mourinho’s time at Real Madrid saw him blessed with one of the best attacking teams ever, one that scored so many goals, won La Liga and lifted the Copa del Rey.

But they never got going in the Champions League, and that was in part thanks to a wonder performance from Robert Lewandowski in 2013.

The Pole scored FOUR in one semi-final night to overturn a first leg defeat and see Dortmund progress to a date with Bayern Munich at Wembley.

Remember that season we spoke about earlier where Chelsea crumbled as champions? Yep, we’re here again.

At White Hart Lane, Chelsea rolled up for the London derby on New Year’s Day and were introduced to a budding young striker called Harry Kane.

He scored twice while Nacer Chadli, Andros Townsend and Danny Rose also netted to make Diego Costa, Eden Hazard and John Terry’s goals worthless.

Mourinho’s time at Old Trafford is best remembered for winning the Europa League in 2017, which got them into the Champions League the following season.

United got through a tough group stage and after drawing the away leg 0-0, just had to beat Sevilla at home to get into the quarter-finals. They didn’t, and were thoroughly outplayed en route to a Wissam Ben Yedder inspired 2-1 defeat.

After taking over at Old Trafford, Mourinho made his return to Stamford Bridge as the opposition manager for the first time.

Things couldn’t really have gone much worse in truth, as Pedro’s goal in the opening minute set the tone for a thumping win for Antonio Conte’s side. 4-0 and embarrassing to say the least.

Yeah, it’s that season of Mourinho at Chelsea once again – it really was a bad one, eh?

This time in the FA Cup fourth round, Chelsea were drawn with League One Bradford at Stamford Bridge. A walk in the park for the Blues, surely?

After racing into a two-goal lead, victory seemed inevitable. But even though the Bantams were 49 places below Chelsea in the league pyramid, they miraculously fought back to score four times – completing the most ‘special’ of cup comebacks.

In Mourinho’s first spell in charge at Chelsea, he truly was special.

The Blues won back-to-back Premier League titles in his first two campaigns, but it wasn’t completely all fun, games and flowers.

But coming up against Middlesbrough, Fabio Rochemback, Stewart Downing and Yakubu got on the scoresheet to hand Mourinho only the third defeat of his Premier League career – with the Portuguese boss admitting “we deserved it” at the final whistle.

Real Madrid CF v Club Atletico de Madrid - Copa del Rey FinalReal Madrid CF v Club Atletico de Madrid - Copa del Rey Final
Jose Mourinho’s Real Madrid side collapsed and lost to their rivals in the cup final | Denis Doyle/Getty Images

Losing a cup final is bad, losing to your city rivals is worse.

Losing to your city rivals in a cup final after taking the lead in the game? Unforgivable.

Add to the mix that you were personally sent off and you have Mourinho’s experience of the 2013 Copa del Rey final pitting Real against Atleti. Ouch.

2-0 up going into the second leg of a Europa League last 16 tie, and fielding a strong lineup just days after tasting defeat in the north London derby? What could go wrong?

Plenty as it turned out.

Mislav Orsic scored one of the best hat-tricks you’re likely to see as the Croatian minnows overturned a first-leg defeat to send Tottenham crashing out of tournament they had celebrated qualifying for so extravagantly.

Matches in world football don’t come any bigger, better, or full of drama than El Clasico.

Not only was this Real Madrid vs Barcelona, it was Jose Mourinho vs Pep Guardiola – two of the very best to stand on the touchline as a coach.

On this occasion, however, there was only thing to celebrate – the brilliance of Barça as they mercilessly tore Real Madrid limb from limb. A 5-0 humbling was not only embarrassing for Mourinho, it is – and remains – the worst defeat he’s ever suffered as a manager.

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