The two clubs are among those battling for the final Champions League spot this season, with Chelsea currently occupying fourth place whereas United have now slipped down to ninth.
Just six points separate the pair, though, and United's chances of returning to the top tier of European competition have been boosted by the news that local rivals Manchester City will be banned for the next two years.
Inconsistency has plagued the campaigns of both Chelsea and United, especially the latter, and both clubs have been tipped to spend heavily in the summer as they look to bridge the gap to Liverpool next season.
Two players in particular will reportedly be at the centre of bidding wars between Monday's opponents as Frank Lampard and Ole Gunnar Solskjaer prepare to go head to head over the signings of Borussia Dortmund winger Jadon Sancho and Lyon striker Moussa Dembele.
While Sancho would command a higher fee and undoubtedly create a bigger buzz given his age and form over the past two seasons, it may well be the signing of Dembele which would prove more important for United.
That is because one of Dembele's biggest strengths this season tallies with one of United's biggest weaknesses - away form.
Only seven Premier League teams have picked up fewer points than United on their travels this season, with Solskjaer's side winning just three times and losing six.
Goalscoring has been the main concern, though; the Red Devils have averaged just one goal per game on the road this term and have been outscored by the likes of Burnley, Aston Villa and even the division's lowest overall scorers Crystal Palace. Only Norwich City, West Ham United, Bournemouth and Watford have scored fewer away goals.
By contrast, the majority of Dembele's 13 league goals this season have come on the road, netting eight times in away games compared to five times at home.
Indeed, the 23-year-old has scored more away goals than any other player in the French top flight, while across Europe's top five leagues only Robert Lewandowski, Timo Werner, Romelu Lukaku, Ciro Immobile, Jamie Vardy, Pierre-Emerick Aubameyang and Raheem Sterling have found the back of the net more often on their travels.
Such an away record would certainly be more welcome at Old Trafford than Stamford Bridge, where Tammy Abraham has an identical home/away goal split to Dembele.
Only Man City and Leicester have outscored Chelsea on the road this term, with the Blues having netted 15 more away goals than United and 11 more than they have managed at home. body check tags ::