Love him or hate him, there’s no disputing that Jose Mourinho has been one of the most successful managers of the last two decades, winning major trophies in England, Italy and Spain.
The Portuguese’s favourite stamping ground though has arguably been the Champions League; Mourinho has led outsiders Porto and Inter Milan to victories in Europe’s biggest competition while also overseeing huge results for Chelsea, Real Madrid and Manchester United too.
Can he now lead Tottenham to glory in the competition? Only time will tell, but if he does so, he’ll have to reach the same heights that he managed in the following 5 historic Champions League performances.
#1 FC Porto vs. Manchester United – Round of 16, 2003-04
The 2003-04 edition of the Champions League, saw Portuguese titleholders and winners of the previous season’s UEFA Cup FC Porto qualify for the knockout stages after finishing in second place in their group behind Real Madrid.
At that point, Jose Mourinho was beginning to garner a reputation as one of the best young managers in the game, but few people expected his side – filled largely with Portuguese players – to overcome Alex Ferguson’s Manchester United in the round of 16.
But that’s exactly what happened, with Mourinho announcing himself to the world as the manager to watch in the 2000’s. Porto were fantastic in their 2-1 victory in the first leg of the tie at the Estadio do Dragao, dominating the match and having 18 shots on goal to United’s 4, despite the Red Devils taking an early lead through Quinton Fortune.
Porto fought back and ended up cementing the win thanks to a brace from Benni McCarthy, and with midfielder Deco in particular controlling the game with his ability on the ball, United became frustrated and saw their captain Roy Keane dismissed for a stamp on goalkeeper Vitor Baia.
The result still left United in with a chance, though – a 1-0 win at Old Trafford would’ve been enough – but in another game low on scoring opportunities, Mourinho had the last laugh. Ferguson’s side took the lead through Paul Scholes' goal in the first half, and then looked to have doubled it when the England man struck again – only for a controversial offside call to chalk the goal off.
But despite United pushing for the killer second goal, Mourinho’s men hung tough – and in the dying seconds of the game, they struck a fatal blow of their own when holding midfielder Costinha pounced on a spilled ball from keeper Tim Howard to prod home, sending the Portuguese side through.
Mourinho’s celebration – sprinting along the touchline at Old Trafford – remains famous today as the moment in which he truly rose to fame – or infamy, depending on your tastes.