Mourinho burst into the British sporting consciousness with his touchline dash and knee-slide at Old Trafford while defeating United en route to Porto winning the 2004 Champions League before having some compelling battles with Sir Alex Ferguson during his first spell with Chelsea.
He also met United with Inter Milan and Real Madrid, who ended Ferguson's bid for a third European Cup last term, and the Portuguese insists the challenge remains even though David Moyes is now in charge.
Mourinho said: "I lost, I won, I drew. I knocked them out of the Champions League, I was knocked out in the Champions League.
"I have everything against them. Maybe I won more than lost. Maybe. But playing Man United - I always say the same - gives me pleasure. I like it.
"Last year we were playing them, in the Champions League knockout stages and everyone in Madrid was with some tension.
"'At the early stage of the Champions we have to play Man United'. I was happy. I like (it).
"I like the stadium, I like the opponent, I like the difficulty of the game. I like it very, very much."
The last-16 tie between United and Real hinged on the controversial dismissal of Nani, but a subplot was Ferguson's decision not to start with Wayne Rooney, who is now a target for Chelsea.
"I wasn't surprised," Mourinho said.
"They have so many attacking options. They have Rooney, Chicharito (Javier Hernandez), (Robin) van Persie, (Ryan) Giggs, Nani, (Danny) Welbeck, (Antonio) Valencia, Ashley Young. So many.
"This season they have (Wilfred) Zaha too. So many that you never know who is going to play."
Whether he plays or not, Rooney is sure to be the focus of attention on Monday, given Mourinho's stated intent to return with a third bid for the striker following the game. United insist Rooney is not for sale.
Rooney may be more than a subplot on this occasion, when there is an opportunity to strike an early blow in the title race.
Given Chelsea will have played a game more, Mourinho has downplayed the significance of a win for his side, even though it would take them six points clear of United.
And in contrast to Spain, where the Barcelona and Real Madrid contests go a long way to deciding the title, Mourinho believes the number of contenders in the Premier League this term mean the impact of the big games is diluted.
"We have six teams (in contention)," Mourinho added. "I keep saying that Man United is the champions and has a fantastic team.
"Man City has an unbelievable squad and, for me, Tottenham has an amazing squad, too.
"After that Liverpool has the history, has the manager, has some players. I don't think Brendan (Rodgers, the Liverpool boss) has the economical conditions to make a huge improvement in his squad.
"Man United or Chelsea (will) lose points, or both. So we are there, all of us."
Following the United clash, Europa League winners Chelsea next play in the UEFA Super Cup, where Mourinho will face Pep Guardiola, once his counterpart at Barcelona and now boss of European champions Bayern Munich.
"The team of Jupp Heynckes (the former Bayern boss) was the strongest team in Europe last season, for sure," Mourinho said.
"And this season they are the same team, with three new players, all of them good, with a new manager, also good.
"Normally they have to be better this season than they were in the previous season."
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- Man United
- Real Madrid
- Wayne Rooney
- Sir Alex Ferguson