Since taking over the Red Devils, the Portuguese has lost four games against the Blues, winning twice -– with both victories coming at Old Trafford.
But, unfortunately for Mourinho, Saturday’s meeting with the Blues comes at Stamford Bridge, where he has experienced different types of defeat.
The first was an embarrassing 4-0 loss in 2016, followed up by a slender 1-0 FA Cup defeat later that season having gone down to 10 men. And last year another 1-0 defeat came as Chelsea made the most of their opportunities.
However, United’s poor recent record at Stamford Bridge is not just down to Mourinho, with the Red Devils without a win since October 2012 when Sir Alex Ferguson’s side beat the Blues -– managed by Roberto Di Matteo –- 3-2.
Unlike Mourinho’s previous three Stamford Bridge defeats to Chelsea, the Portuguese faces a new man in the opposing dugout with Maurizio Sarri now in charge of the Blues.
Maurizio Sarri's Chelsea have enjoyed a good start this season
Sarri’s side have started the season well, currently joint-top of the Premier League with 20 points alongside Manchester City and Liverpool, unbeaten after eight games. In contrast, United are eighth having lost three of their opening eight matches.
But how can Mourinho be his best Mourinho and suffocate Sarriball to hand Chelsea their first defeat of the season?
In the previous two seasons against Chelsea, Mourinho has preferred to line his United side up in 3-5-2 formation to combat the Blues’ own three-man central defence favoured by Antonio Conte.
But now Conte has gone and Sarri has brought the 4-3-3 back to the Bridge, meaning a change in formation may be likely for Mourinho too to try and combat Chelsea’s exciting, attacking style of play.
Mourinho has already tried a 3-5-2 this season when United took on Tottenham Hotspur at home but the formation was picked apart by Spurs in a 3-0 humiliation at Old Trafford, with the away side countering hard and making the most of the high wing-backs.
It may be better for Mourinho to take some inspiration from his past matches against the likes of Liverpool and Manchester City, who employ somewhat similar tactics to Chelsea under Sarri.
The Portuguese has had the most success with a 4-3-3 formation, going unbeaten against Liverpool and City during his time at Old Trafford, and it may be the best option to beat Chelsea.
Sarri’s style of play sees Chelsea focus on the wings heavily, pushing the attacking play down the left side of the pitch with his players on that flank seeing a lot of the ball while the right-sided players are reliant on their movement and making an impact with fewer touches.
Though a five-man defence may be the better option in limiting Hazard, the use of wing-backs could cause detriment to United, with Sarri-ball enticing opposition defenders to push up the pitch, opening spaces for more attacking players to move into and punish.
A three-man central midfield will give United balance in both defence and attack, which United can use to get at a Chelsea defence still showing signs of weakness given their high line – something an attacking trio can make the most of too.
The starting XI
The formation is all set, now it’s time to nail down the players to make the most of the way United will line up.
Jose Mourinho has his favourites at Manchester United especially when it comes to shutting teams down by frustrating their star attacking players. The man he relies upon most is midfielder Marouane Fellaini.
By playing Fellaini in a midfield trio alongside Nemanja Matic and Paul Pogba, the Belgian can be the transition between defence and attack, helping Matic when Chelsea are pushing and getting forward to cause a problem from set pieces when United are in the ascendancy.
Defensively, Mourinho seems to have a set back five this season when all of his players are fit. In goal, David de Gea is irreplaceable while Luke Shaw and Antonio Valencia are the favoured full-backs on form and should continue.
The centre-back pairing is less impressive but Mourinho is seemingly unhappy with the way Eric Bailly and Victor Lindelof have been playing, with the former being an early casualty in United’s 3-2 win over Newcastle United in which the Red Devils went two goals down after just 10 minutes.
Up front, Alexis Sanchez came off the bench to have a massive impact against Newcastle, arguably pushing himself ahead of Anthony Martial once more -– although he also scored in that game.
Marcus Rashford impressed on international duty with England and should likely be rewarded while Romelu Lukaku will be a certainty to start unless injured.
The players and formation will count for nought, however, if Mourinho does not get his tactics right.
Priority number one would be keeping a hold on Premier League top scorer Eden Hazard, who has been in scintillating form under Sarri with seven goals in eight appearances so far.
In the past, Mourinho has deployed the likes of Scott McTominay and Ander Herrera as the midfield destroyer against teams like Chelsea, but both have rarely been called upon this season whereas Fellaini seems to be becoming more important to United week-by-week.
Jose Mourinho's side have struggled against Chelsea at Stamford Bridge
Fellaini’s place in the team would also be important to how Pogba plays, giving the Frenchman more freedom up the pitch. The Belgian’s role in Pogba’s future was clearest in United’s 1-1 draw against Wolves in September.
When Fellaini was instructed to sit back and defend, almost dropping to a third centre-back at times, Pogba flourished, playing an important part as United went up the pitch. Yet when the Belgian got forward, Pogba’s performance dropped having to try and influence the game from deep -– something N’Golo Kante would sweep up and prevent with ease.
Mourinho has made a name for himself for extremely defensive tactics when taking on the bigger teams, with jokes flowing regard buses and parking, especially away from home.
But it will be United’s best option against Chelsea on Saturday, ensuring the back four focus on their defending alongside Matic and Fellaini, potentially settling as a back five -– or even six -– when defending.
This will require the forwards to do most of the attacking with little help from their full-backs, but with Pogba getting involved too, they could still cause problems –- with one of Sanchez, Lukaku or Rashford looking to put pressure on the weakness of Chelsea’s defence, David Luiz.