Roman Abramovich's acquisition of the West London club in 2003 was the catalyst for these sides to initiate a rivalry that is still ongoing, due to the pair's Premier League triumphs.
Chelsea's five titles in the PL era are only eclipsed by the Red Devils' 13, each winning five since the Russian billionaire arrived.
Ole Gunnar Solskjaer ended an over six-year wait for a win at the Bridge during his interim period in February 2018 and has won on his two following visits, meaning Man United haven't lost at Sunday's venue in their last four trips.
Planet Sport takes a look at the Red Devils' best performances against the Blues down the years.
Man United and Chelsea have met 188 times across 115 years, mostly contesting in England's top tier.
The Red Devils boast an impressive record of 81 victories, losing 55 times and drawing on the remaining 52 occasions, one of which being this season's goalless stalemate at Old Trafford.
Solskjaer has had the better of the men from Stamford Bridge since returning to Manchester as manager, boasting a record of four wins, two draws and one defeat in all competitions - the latter being last year's FA Cup semi-final.
Tuchel and the Norwegian have met four times, including this twice in this campaign's UEFA Champions League group phase, each winning their respective away game, the same outcomes as the historic round-of-16 clash between Man United and Paris Saint-Germain in 2019.
There's plenty of history between the teams without the managerial pair, however.
Top five performances
Manchester United 1-1 Chelsea (6-5 on penalties)
UEFA Champions League final
May 21, 2008
For our first entry, we're looking at the most famous meeting between these teams on the biggest stage of all.
In Russia, almost 13 years ago, tears rained on the Blues while the Red Devils reigned over Europe for the third time.
For context, England's two best sides of the era were separated by just two points at the end of the preceding Premier League season, as Man United won their second title on the bounce and Avram Grant's men narrowly fell short.
They did here, too, as Sir Alex Ferguson and co edged a terrifically tense match on penalties.
A trademark Cristiano Ronaldo header broke the deadlock after 26 minutes before Frank Lampard made the most of the slippery conditions to equalise seconds prior to half-time.
Seventy-five minutes of torture for the travelling supporters ensued and Chelsea must've thought the night was theirs when, despite Didier Drogba being sent off in extra-time, Ronaldo missed in the shootout and captain John Terry stepped up for the chance to win it from the spot.
You know the rest; he slipped and so did his beloved club's chances of lifting the European Cup, as Edwin van der Sar saved from Nicolas Anelka and, in the immortal words of Clive Tyldesley, it was 'United again.'
Manchester United 3-0 Chelsea
January 11, 2009
To the bread and butter of domestic football now, and when the Red Devils brushed the Blues aside with this rampant display on their way to a third consecutive title.
A largely uneventful first half was ignited in injury time as Man United's cheeky corner routine resulted in Ronaldo nodding in, but referee Howard Webb ruled it out - only for the retaken attempt to result in Nemanja Vidic heading in from Dimitar Berbatov's flick on.
Good work down the left flank from CR7 and Patrice Evra after the interval set up Wayne Rooney to ruthlessly increase the Red Devils' advantage, before Berbatov bagged one himself.
Rafael Benitez's Liverpool were being hunted down and would be by the time May came around, as title number 18 came to the red side of Manchester.
Manchester United 2-1 Chelsea
May 8, 2011
Having met in the UCL quarter-finals a month earlier, Man United triumphed over Chelsea for the second time in 2010/11 and went within a point of a record 19th English title as they sunk the chasing champions.
Javier Hernandez needed just 36 seconds to open the scoring before Vidic doubled the Red Devils' lead on 23 minutes, heading home past Petr Cech.
The fixture followed 2010's title-deciding clash - as the trophy went to London - and Ferguson's Red Devils viciously enacted their revenge after going into the game with a three-point lead and three games to play.
Lampard's instinctive second-half effort was ultimately rendered a consolation and Man United had all but reclaimed their crown.
Manchester United 2-0 Chelsea
April 16, 2017
Far from the glory years of the SAF era, former Blues boss Jose Mourinho inflicted a late scare on the eventual champions four seasons ago.
Antonio Conte's outfit were stumbling in the springtime, giving Tottenham Hotspur hope of usurping them at the top, and stuttered again, thanks to Marcus Rashford and an Ander Herrera midfield masterclass.
The Spaniard stuck to Eden Hazard like glue, played in Rashford to strike after just seven minutes and scored himself four minutes post-restart.
Conte and co would go on to win the club's fifth title as the Red Devils dwelled in sixth spot, but it was a stunning shock result from Mourinho's men.
Manchester United 4-0 Chelsea
August 11, 2019
Solskjaer's side got off to a flyer on the opening day of last term, as Rashford continued in his decent individual record of five goals and three assists in 12 games against Chelsea.
A brace from the now national treasure and one each from Anthony Martial and new signing Daniel James meant it was the perfect start to '19/20 at Old Trafford.
Contrastingly, Super Frank's short time as gaffer began horribly in spite of a close first half.
He tasted fresh pain back at the Theatre of Dreams, losing this time as a manager - like he would twice more at home over the following few months.
Only goal difference meant Man United finished above Chelsea in the top four come July and things haven't changed much this time around.
Tip of the Fixture
Another 0-0 draw like the drab October meeting is priced at 9/1 with Paddy Power, with Tuchel's team having only conceded two goals in eight games since he took the hot seat.
(Odds correct at time of writing, subject to change)