The Portuguese faced his worst career defeat in charge of AS Roma in the UEFA Conference League.

Throughout his decorated career, Jose Mourinho has established himself as a pragmatic yet yielding manager. Using a relatively defensive brand of football, the Portuguese has earned plaudits for resisting and overcoming even the most offensive tactics. Due to this very reason, it is uncommon to see a Mourinho-managed side getting involved in high-scoring matches, forget about high-conceding ones.

There are, however, a few fixtures that defy the normal. Here are five defeats that stand out as some of the longest nights in the career of The Special One.

5. Liverpool 4-1 Chelsea (2007)

Only Frank Lampard managed to score for Chelsea in the penalty shootout

Albeit unconventional, one of the heaviest defeats in the managerial career of Jose Mourinho came in a penalty shootout. Liverpool defeated the Blues 4-1 in the penalties, after a 1-1 stalemate in two legs of the Champions League semi-finals. Daniel Agger’s goal in the return leg at Anfield cancelled out Joe Cole’s first leg winner to force penalties.

Despite both legs being toe-to-toe in terms of competition, the penalty shootout was as one-sided as it gets. Arjen Robben and Njitap Geremi missed their spot kicks, while the Reds scored all four to book a final spot. Only Frank Lampard scored for the Blues, and Dirk Kuyt’s kick took Liverpool a step closer to the glory.

4. Borussia Dortmund 4-1 Real Madrid (2013)

The 2013 edition of the UEFA Champions League is still talked about for the German dominance. Borussia Dortmund eliminated Real Madrid to book a berth in the final with Bayern Munich, who thumped FC Barcelona. In the first leg against Real Madrid, managed by Jose Mourinho at the time, Dortmund netted four past Diego Lopez.

This match displayed the highest number of goals a player has scored against a Jose Mourinho-managed side in a single game

In addition to being one of Mourinho’s biggest defeats, the night signified the rise of Robert Lewandowski. The Polish striker scored a poker, taking his tally to 10 in for the 2012/13 edition. This remains as the the highest number of goals that a player has scored against a Jose Mourinho-managed side in a single game. Cristiano Ronaldo’s 43 minute equalizer was cancelled out just seven minutes later, and Lewandowski scored twice in 27 more minutes.

Although Los Blancos put on a brave fight in the return leg and missed out the final spot on away goals, this game did all the damage. On hindsight, this defeat is looked upon as one of the most defining moments in Mourinho’s last-minute fallout at Real Madrid.

3. Chelsea 4-0 Manchester United (2016)

When Jose Mourinho returned to Stamford Bridge in 2016, it did not end like a regular day in any means. Suffering his biggest defeat in the Premier League against his former club, Jose Mourinho looked helpless as Chelsea registered a 4-0 win.

N’Golo Kante’s solo goal was the highlight of the match

Having an in-form Zlatan Ibrahimovic upfront, accompanied by Marcus Rashford and Jesse Lingard, United’s attack looked toothless on the night. Antonio Conte’s Blues opened up in the very first minute via Pedro, and Gary Cahill made it 2-0 just after the 20th minute mark. Eden Hazard did further damage with a right-footed shot past David de Gea as the clock hit the 62nd minute.

However, the match-defining moment came in the 70th minute, when N’Golo Kante walked past the Manchester United defence with ease. The moment was emblematic of how helpless Mourinho’s men were on the night, standing merely like cones in the French midfielder’s run.

2. FC Barcelona 5-0 Real Madrid (2010)

The first one of the epic El Clasico that embarked Pep Guardiola-Jose Mourinho rivalry was the latter’s biggest loss as the Madrid manager. In a sold out night at the Camp Nou, the Blaugrana pulled off a Manita, putting five past Real Madrid who were looking to get off the Galactico hangover.

Lionel Messi shone for the Blaugrana that night

A brace from David Villa, topped by goals from Pedro, Xavi, and late substitute Jeffren blew Mourinho’s Madrid apart. Despite not being on the scoresheet, Lionel Messi was the main man for Barcelona, and stole the spotlight from his counterpart Cristiano Ronaldo on the night. Accumulating two assists, both for Villa, Messi’s false-nine play was too hard for Mourinho’s side to contain.

It was not just the flurry of goals which made the fixture memorable. Sergio Ramos’ last-minute sending off for an infamous foul on Messi was just one of many vile incidents that unfolded. 12 yellow cards were shown during the match, which later came to be a regular sight whenever the two sides met.

1. FK Bodo/Glimt 6-1 AS Roma (2021)

The biggest managerial loss of Jose Mourinho came in a match where it was least expected. Facing Norwegian side FK Bodo/Glimt in the UEFA Conference League, Roma lost 6-1. Roma were humiliated on all fronts, and the scoreline was just one reflection of the horrendous night at the Aspmyra Stadion.

This match marked Mourinho’s biggest defeat in his managerial career

Although the side entered the fixture as the most successful and decorated side in the group, an eighth-minute goal from Erik Botheim, who went on to add another in the 52nd, started piling worries on Mourinho’s side. Although Carles Perez’s 28th minute strike brought the tie to 2-1, it was the closest occasion on the night.

The Serie A side went on to concede four goals in the second half, including a brace by Ola Solbakken. Mourinho’s side, valued more than €400m more than their opponents registered fewer shots than Glimt. Under Jose Mourinho, AS Roma is currently fourth on the Serie A table and have already lost thrice in eight league games.

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