Jose Mourinho’s Porto side travelled to Manchester for their Champions League last 16 second-leg, after a bad-tempered home tie in which the Portuguese outfit had triumphed 2-1.
It looked as if United were set to progress having taken a 1-0 lead through Paul Scholes, but a last-minute goal from Costinha knocked Ferguson’s team out of the competition.
Mourinho had already built a reputation by then as a fine young manager, yet it was the image of him celebrating down the Old Trafford touchline that cemented him in the consciousness of the English football public.
4. Manchester United 1 Chelsea 2 - 2005
Mourinho’s first Premier League game at Chelsea came against Manchester United (a 1-0 victory), but it was this Carling Cup tie later in the same season, that saw the first domestic clash that really mattered.
United had ground out a 0-0 draw at Stamford Bridge, but couldn’t get the result they wanted at home. Frank Lampard gave the visitors the lead and though Ryan Giggs scored a brilliant equaliser, Damien Duff would grab the winner for Chelsea after an error by Tim Howard in the United goal.
Chelsea had reached their first final under Mourinho, which they would go on to win. That initial Carling Cup is now considered to be crucial to the way Mourinho established a winning culture at the club and the legacy that followed.
3. Chelsea 3 Manchester United 0 - 2006
Jose Mourinho won the Premier League in his first season. There wasn’t many ways to top that, but by clinching another title in his second season with a victory over Manchester United, he achieved it.
Ferguson had seen his team triumph for the first time against a Mourinho side earlier in the season, breaking a run of six games without a win.
Lightning was not about to strike twice. Needing only a point to win the Premier League, Chelsea took all three, thanks to goals from William Gallas, Joe Cole and Ricardo Carvalho.
2. Chelsea 1 Manchester United 0 - 2007
Manchester United drew both of their games with Chelsea en-route to winning the 2006-07 Premier League, setting up an FA Cup Final where Alex Ferguson had the chance to get his hands on another double.
Jose Mourinho had other ideas. His Chelsea side weren’t the better team in the final, yet still triumphed, as Didier Drogba scored the final’s only goal in extra-time.
1. Manchester United 2 Inter Milan 0 - 2009
This list rather highlights the fact that Jose Mourinho has generally come out on top when his teams have met Alex Ferguson’s, but don’t expect the United manager to be losing any sleep over that.
For starters, he’s not a man that struggles for confidence and secondly, his United side beat Mourinho’s Inter Milan in the last game between the two managers.
After a 0-0 draw at the San Siro, Manchester United knocked Inter out of the Champions League at the last 16 stage. The goals were scored by Nemanja Vidic and a former United player by the name of Cristiano Ronaldo. Now whatever happened to him?