Mourinho was relieved of his duties last December, and it will be a little under a year to the day that the Special One heads back to the Theatre of Dreams in charge of a new club.
Tottenham have enjoyed the so-called 'new manager bounce' with three wins out of three for Mourinho to leave them fifth in the Premier League table - though that says as much about the likes of Arsenal and United as it does about Spurs.
Mourinho's return could not come at a worse time for Solskjaer, who contrived to draw against Sheffield United (3-3) and Aston Villa (2-2) with Mauricio Pochettino waiting in the wings.
While United are keen to back Solskjaer's long-term vision for the club, a humbling home defeat to Mourinho of all people could force Ed Woodward to pull the trigger once again in December.
Premier League preview
Manchester United vs Tottenham
Venue: Old Trafford
Date: Wednesday, 4 December, 2019
Kick-off time: 7:30pm GMT
Manchester United 1-1 Tottenham: Despite his warm words for United of late, Mourinho would dearly love to inflict a convincing defeat on them on their own turf.
The saving grace for United is that Solskjaer and his side are better in big games, and should have a decent game plan - so a draw is most likely.
Betting tips and odds via Betfair exchange
- Man Utd to win: 7/4
- Tottenham to win: 9/5
- Draw: Between 13/5
Man Utd win
Odds provided by Betfair. Click here to place a bet. Odds correct as of December 2.
For ticket information click here to head to United's official website.
Spurs have announced that season ticket holders with 214 or more ticketing points who applied by the deadline will receive a ticket. Click here for more information.
Solskjaer is hoping at least one of Scott McTominay and Paul Pogba will return from injury, with the Scot the more likely of the pair to start.
Nemanja Matic, Eric Bailly and Timothy Fosu-Mensah are back in training but lacking match fitness, while Diogo Dalot and Marcos Rojo are still out.
The United boss could be tempted to revert to a back three with Axel Tuanzebe coming in after seeing his side concede five against Sheffield United and Villa.
Mourinho will be missing Hugo Lloris until the New Year, while Michel Vorm's absence means Paulo Gazzaniga is certain to keep his starting role in goal.
Erik Lamela is sidelined with a thigh injury along with Ben Davies (ankle).
Despite three wins out of three, Mourinho has concerns over a defence which has conceded two goals in each of those matches.
It will be fascinating to see whether the Portuguese coach attempts to constrict such a high-stakes game in his usual manner, or if he sticks with how Spurs are currently winning - by forgetting about defending and looking to outgun a similarly shaky United back line.
Man Utd XI: De Gea; Lindelof, Maguire, Tuanzebe; Wan-Bissaka, McTominay, Fred, Williams; James, Martial, Rashford
Tottenham XI: Gazzaniga; Aurier, Sanchez, Alderweireld, Vertonghen; Ndombele, Dier; Sissoko, Dele Alli, Son; Kane
How to watch Man Utd vs Tottenham
Along with every Premier League match in gameweek 15, the game will be available to live stream online on Amazon Prime.
Existing and new Prime members can watch on devices using the Prime Video app, across mobile, Fire TV, games consoles, Virgin’s V6 TV Box, BT TV, TalkTalk TV, Apple TV, Chromecast, online and more.
You can follow all the action on Standard Sport's LIVE match blog with James Robson and Dan Kilpatrick at Old Trafford.
Head to head (H2H) results history
United have a great record against Tottenham with 91 wins to Spurs' 52 victories, and 48 draws.
However, their recent history is more evenly split with the last nine meetings alternating between Spurs and United wins.
Last season, Spurs thrashed United 3-0 on their last visit to Old Trafford - a result which sparked the beginning of the end for Mourinho in Manchester - but the Red Devils got their own back with a 1-0 win in north London the last time they met.