1) Pep Guardiola
There is no manager in the footballing world who has a better record against Mourinho than Pep Guardiola. But this record holds more significance than others for Jose. Their rivalry goes way back and there is a lot of history between the two.
The two were initially friends at Barca where Jose was assistant manager. They parted ways later, but in 2008, a new coach was set to be appointed at the Catalan club. Jose thought he would get it because of his association with Barca but they ended up giving it to Guardiola.
Mourinho was adamant to prove his former employers they were wrong and went to Real Madrid. He learned a harsh lesson in his very first Clasico after his Madrid team received a 5-0 drubbing.
Jose was the only one to break Barca’s dominance over the La Liga title in Pep’s last season there but his overall record does not make for good reading. So in 2016, when it was announced Pep would be taking over at Manchester City and Jose at United people marked down their calendars for the first Manchester derby.
Unfortunately for Mourinho, his arch nemesis once again got the better of him as United slumped to a 2-1 defeat at Old Trafford. In all the two have faced each other 17 times. Pep has 8 Wins to his name and Jose only has 3.
The Portuguese has a lot of catching up to do, but time is on his side,