Mourinho against one of two English opponents he's failed to beat.

The 10 clubs Jose Mourinho has faced and never won against

Jose Mourinho is one of the greatest football managers of all time, but that doesn’t mean he’s beaten every single opponent that’s crossed his path.

Starting out in his native Portugal, Mourinho has managed the likes of Chelsea, Real Madrid, Inter Milan and Manchester United, usually winning silverware wherever he’s been employed.

But we’ve dug into the archives and have identified the 10 opponents the Special One has never managed to get the better of.

Real Madrid

It’s true – Mourinho has never beaten the club he managed between 2010 and 2013. It’s a football fact that’ll impress your mates down the pub if nothing else.

He faced Madrid four times in the Champions League with Porto, drawing once and losing the remaining three, while he also couldn’t get them with Manchester United in the 2017 UEFA Super Cup final.

Some Madridistas will grumble that Mourinho settled for an inside job instead, burning his bridges during a final acrimonious season at the Bernabeu. Sounds about right.

Jose Mourinho Signings at Real Madrid featuring Mesut Ozil

READ: Where are they now? Jose Mourinho’s 15 signings at Real Madrid


Venice is one of the biggest tourist destinations in Europe, but its local football club have rarely troubled the Serie A big boys.

Despite their limited status, Mourinho couldn’t beat the Venetians with Roma in 2021-22. The Special One lost 3-2 in Venice before labouring to a 1-1 draw back at the Stadio Olimpico.

Venezia are back in Serie A next season, but (a possibly traumatised) Mourinho has long since departed.


Home to one of the biggest stadiums in Italy, Bari is the ninth biggest city in the peninsula but stubbornly underachieves at football.

But Bari held Mourinho’s all-conquering Internazionale to two draws in the 2009-10 season, a season where they finished 10th in Serie A.

They finished rock bottom 12 months later and went bankrupt three years after that. Whoops.

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RB Leipzig

Now regulars in the Champions League, RB Leipzig can usually be relied upon to give any opponent a decent game – as Mourinho found out with Tottenham in 2009-10.

Their last 16 match was expected to be a close affair, but the east Germans won 1-0 in London before spanking Mourinho’s Spurs 3-0 in the return leg.

“We all believed but we know that in this moment it’s very difficult. They are a very strong side,” the vanquished Portuguese said afterwards. “They deserve to go through.”

Sparta Prague

As the Champions League riches have increased, one of the many consequences is that you just don’t see clubs like Sparta Prague beyond a succession of group-stage drubbings.

But the Czech giants used to be very handy in Europe’s premier competition, inflicting a 2-0 defeat on Porto in the second group stage back in 2002.

Yes, that’s right. There used to be two Champions League group stages, an abomination that was axed in the interest of player welfare. Good to see UEFA have kept to the same principles two decades on…


Mourinho’s first spell at Chelsea was one of the most iconic managerial reigns of the modern era; never mind all the trophies, the belligerent manager and newly-minted football club were absolutely perfect for each other.

But it all ended inauspiciously with a 1-1 Champions League draw against Rosenborg in front of just 24,973 at Stamford Bridge in September 2007.

“Of course I am alarmed,” Mourinho said afterwards. “I am not happy.” He was even less happy when ‘mutual consented’ out the door 24 hours later.

Bristol City

Mourinho was generally decent in the cups at Manchester United, winning both the League Cup and Europa League in 2017 while reaching the FA Cup final one year later.

But his United side, which included the likes of Paul Pogba, Zlatan Ibrahimovic and Marcus Rashford, suffered a humiliating League Cup quarter-final exit at Championship outfit Bristol City in December 2017.

Goals from Joe Bryan and Korey Smith sealed one of the most famous wins in City’s history and a real taste of what one of English football’s most notorious sleeping giants could achieve in the right hands.

Bradford City

Bradford City coming from two goals behind to win 4-2 at Stamford Bridge in January 2015 is one of the most memorable upsets in FA Cup history

READ: Giant killings: How Bradford crushed Jose Mourinho’s Chelsea at the Bridge

Halmstads BK

Mourinho has only faced Halmstads once – in the first round of the UEFA Cup (ask your dad) in September 2000 as manager of Benfica.

The Special One was weeks into his first managerial job when he drew 2-2 with the Swedish side at the old Estadio da Luz.

Sadly, Benfica had lost the first leg 2-1 and crashed out of the competition. Mourinho would have better European campaigns than this.

Deportivo Aves

Mourinho only lasted three months at Benfica before taking over at fellow Portuguese side Uniao de Leiria.

In what must be one of the more forgettable matches in football history, the future legend eeked out a goalless draw against Deportivo Aves in May 2001.

Aves no longer exist in their current form. Due to unpaid debts to other clubs, the club received a transfer ban from FIFA in 2020 – which it sidestepped by founding new entity Clube Desportivo das Aves 1930. Clever.