The home side, who head into the midweek clash on a run of three consecutive victories against the Terrors, will look to continue in the same vein and march on in the competition.
Match preview
Livingston fell to a second consecutive defeat for the first time since losing four in a row back in April as they were thrashed 5-0 by Aberdeen at Pittodrie last Saturday.
In a game where Jack Fitzwater received his marching orders, goals from Ross McCrorie, Vicente Besuijen, Ryan Duncan and a brace from Bojan Miovski saw the hosts ease to their third win of the season.
Prior to that, the Lions were denied a third league win on the bounce on August 20 when they fell to a 1-0 defeat at the hands of Motherwell courtesy of Kevin van Veen's 68th-minute penalty.
David Martindale's men now turn their attention to the Scottish League Cup, where they scaled through the qualifiers as one of the three best group runners-up after picking up nine points to finish second in Group G, two points off first-placed Inverness CT.
Livingston, who wrapped up the qualifiers with two successive wins, will be looking to go one step further than their 2020-21 cup run where they went all the way before losing 1-0 against St. Johnstone in the final.
Just seven games into his reign as head coach of Dundee United, it is safe to say that Jack Ross's future at the helm hinges on the outcome of Wednesday's game as the 46-year-old watched his side get massacred 9-0 by a rampant Celtic side last weekend.
Ange Postecoglou's men simply ran riot at the Tannadice Park as Japanese forward Kyogo Furuhashi and strike partner Liel Abada both scored hat-tricks to hand the Bhoys their fourth win in five games.
Just 17 days ago, the Terrors were condemned to their biggest-ever defeat in their 113-year history as they were thrashed 7-0 by AZ Alkmaar in the second leg of their Europa Conference League third qualifying round clash at the AFAS Stadion.
Dundee United have now lost each of their last five games across all competitions, scoring just once and shipping a staggering 24 goals since their 1-0 first-leg victory over AZ Alkmaar in the Europa Conference League qualifiers on August 4.
While Ross will hope that his side can end this dry spell and come away with the desired result on Wednesday, next up is an opposing side who have won each of the last three meetings between the teams and are unbeaten at home in their last six encounters.
Livingston Scottish League Cup form:
Livingston form (all competitions):
Dundee United form (all competitions):
Team News
Livingston will take to the pitch without the services of former Leicester City defender Tom Parkes, who could miss up to nine months through a severe knee injury.
Fellow defender Morgan Boyes has been out of action since May, and while the Welshman is nearing his return to full fitness, he will play no part in the midweek clash.
Martindale will also be unable to call upon Bruce Anderson, who picked up an injury in the game against Hibernian on August 13.
Meanwhile, Dundee United will be without the services of 22-year-old forward Logan Chalmers, who has missed the last eight games through injury.
Veteran midfielder Peter Pawlett is also out of contention for the midweek match as the 31-year-old continues his journey to full fitness after suffering a long-term injury back in February.
Livingston possible starting lineup:
George; Devlin, Parkes, Obileye, Montano; Omeonga, Holt, Kelly; Shinnie, Pittman; Nouble
Dundee United possible starting lineup:
Eriksson; Smith, Edwards, Mulgrew, Behich; McGrath, Levitt, Harkes; Watt, Fletcher, Middleton
We say: Livingston 2-0 Dundee United
Dundee United head into Wednesday on a dire run and will be looking to restore some pride following their heavy defeat to Celtic. However, they take a trip to the bogey Almondvale Stadium, where they are winless in their last six visits. We are backing Livingston to bounce back from their slump and come out on top in this one, albeit by a slender margin.