Why Jose Mourinho has revelled so much in beating Manchester United over the last 20 years

When it comes to sticking two fingers up at Jose Mourinho has been doing it for over two decades.

will be hugely motivated in Thursday’s Europa League clash with his old club and beating United has helped shape his career. He’s upset them with Porto, Chelsea, and Tottenham and he hopes to throw another spanner in the works when his Fenerbahce side tackle United in Istanbul.

He will know that is fighting for his life at Old Trafford and how a win for Fenerbahce would push the Dutchman closer to the exit.

That will only be a greater incentive for Mourinho and he has revelled in upsetting opponents all his career.

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Mourinho first cost United in the 2004 when Costinha’s last-minute equaliser at Old Trafford turned the tie on its head as Porto went through 3-2 on aggregate. Mourinho sprinted from his technical area to join in the celebrations in an iconic moment to introduce himself to English football.

He guided Porto to the 2004 Champions League and arrived at that summer, calling himself the “Special One”. He piled more and United as he took winning the Premier League to ridiculously high standards, losing just once in 2005 in that record-breaking season, amassing 95 points.

Mourinho added to United’s pain, beating them in the Carling Cup semi-finals in 2005 before landing another title at their expense in 2006. He denied them a Double in 2007 when his Chelsea side beat United in the FA Cup Final, thanks to Didier Drogba’s extra-time goal.

Ferguson did get some revenge when United knocked his Inter Milan side out of the 2009 Champions League on their way to the final. That was a rare success for United over Mourinho and the Portuguese continued his winning streak, dumping Ferguson’s side out of the Champions League in 2013 in his farewell season.

Mourinho hoped to succeed Ferguson at United and deliberately downplayed his success with Real, in stark contrast to how he behaved when he won with Porto. Instead, United turned to David Moyes, feeling he would be a Fergie mini me, leaving Mourinho to return to Chelsea.

It was United’s loss as they entered the wilderness under Moyes and Mourinho beat United again on the way to lifting his third Premier League crown with Chelsea in 2015. But the Special One’s powers were waning at Chelsea and he was sacked for a second time at Stamford Bridge that December as the Blues struggled.

That allowed him to go to United in 2016 and his two full seasons stand out in the 11 campaigns since Ferguson retired. He lifted the League Cup and the Europa League in his first campaign in 2017 and United were runners-up in the 2018 Premier League race.

Manchester City were finding their groove under Pep Guardiola and Mourinho claims that second place was one of his best achievements. But he was gone that December as United stumbled and they and him were never quite the same.

He in the behind-closed-doors days of Covid and that was proved to be his last hurrah over United.

That is until Thursday night.

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