Mourinho has lost all three away games against the Blues to date, with the Red Devils in fact not picking up a win at Stamford Bridge since 2012 under Sir Alex Ferguson.
While indicative of United's wider struggles in the post-Ferguson era, Chelsea have long been a bogey team for United - with only the Blues and Brighton beating the Red Devils more times than they've lost to them.
Having tasted so much success with Chelsea, Mourinho is still trying to win over Manchester and after a mixed start to the season was saved significant blushes last time out when United came from two goals down to beat Newcastle 3-2.
As the Red Devils desperately try to find some consistency, the Blues have in comparison been cruising under new manager Maurizio Sarri.
Yet to lose in the league and second only on goal difference, Chelsea have looked sharp so far this season with Eden Hazard leading the way as top scorer and the first player to record 10 goal involvements in the competition.
Striker Olivier Giroud has also been pivotal and has gone from scorer to provider with his four assists more than any other player.
Should the Blues avoid defeat against United, it will mark the third time they've gone nine games undefeated to start a season. The only other times they've done so were in 2005-06 and 2014-15 under Jose Mourinho when they'd go on to win the title both times.
That success may almost seem like a lifetime ago for a stressed out Special One, who must defy the odds, form and history to seal what would be a stunning victory for a Manchester United side feeling the blues.