One side are slipping further into crisis, whilst the other are climbing out of a perceived problematic period.
The hosts are engineered by the 'Special One', whilst the visitors have recently been taken over by the 'Next Special One'.
A match that pits the wits of two Portugese managers with varying levels of experience but a common goal across the two legs, a place at Wembley for the EFL Cup Final.
Form favours the hosts
Whilst the Red Devils are undefeated in 14 matches, winning their last eight in a row, the Tigers have only won three matches in 90 minutes since August, all of which were formulated in up competitions.
Inevitably, Hull took a leap of faith to part ways with struggling manager and former United player and coach Mike Phelan, before hiring 39-year old Silva last week.
The ex-Olympiacos and Sporting Lisbon boss has already been compared to Mourinho for his outgoing nature and ability to lead teams to glory. Yet Silva has responded to the similarities by simply stating: "I am Marco Silva, not the Special One."
Despite some adjustments tightening up areas of Hull's play during their FA Cup win on Saturday, Silva will have to mastermind a sensational display if his squad are going to overhaul the qualities of United over two legs.
Not only does Hull's form work against them, but so does their record against the Salford club. Man United have won 11 of their last 12 matches against Hull, drawing the other. The Tigers have only defeated United once at Old Trafford, all of 65 years ago.
Questions posed for both bosses
Both managers will offer intriguing starting elevens at kick-off on Tuesday evening.
Mourinho made nine changes at the weekend in the FA Cup and will decide whether to start Wayne Rooney who equalled Sir Bobby Charlton's goalscoring record for United against Reading.
With a crunch league match against Liverpool coming up on Sunday, Mourinho will have to decide how much respect he can afford Hull whilst ensuring his players are fresh and ready for another crucial encounter.
The hosts will definitely be without Eric Bailly, who is away with Ivory Coast at the African Cup of Nations, and potentially the services of Marcos Rojo with a muscle complaint.
Silva has numerous concerns in defence that resulted in Tom Huddlestone and Jake Livermore forming a makeshift partnership at the centre of the back four at the weekend.
Harry Maguire and Michael Dawson face late fitness tests, whilst Curtis Davies, Ahmed Elmohamady, Moses Odubajo and Alex Bruce are all unavailable.
Hull are also short of options up front with Will Keane and Dieumerci Mbokani absent and Abel Hernandez lacking match fitness to last the entirety of the game.
On paper 14-time League Cup semi-finalists United will be heavy favourites against a Hull side making their debut in this stage of the competition. Yet a sturdy Hull performance could keep them in touch before the away leg at the KCOM Stadium in two weeks' time.