The hosts, who are bottom of the table, trail the visitors by three points but with a superior goal difference, yet victory for Kilmarnock would leave Dundee United on the brink of relegation.
Match preview
Having put together a three-match winning streak in April, Dundee United looked to be well on course for survival under the recently-appointed Jim Goodwin.
However, losing the same amount of games in succession has changed the equation for the worse, the Terrors now back at the foot of the table with two fixtures left.
With a trip to resurgent Motherwell to come on the final day, Dundee United are under huge pressure to get another three points on the board against a direct rival.
At this point, Goodwin and his squad would probably take a relegation playoff, but victory on Wednesday could prove decisive with Kilmarnock and 11th-placed Ross County meeting on Saturday.
Aside from recently losing 2-1 to Ross County, Goodwin's side have been relatively impressive on home territory, collecting seven points from the three games preceding that defeat.
From Kilmarnock's perspective, winning three of their last seven matches has been enough to move the club into 10th ahead of facing the two points below them.
Going down 1-0 to St Johnstone last time out came as a blow, although Derek McInnes may take the positives from not conceding with 10 men for over half the match.
Since losing 4-1 at home to Celtic in April, Kilmarnock have conceded just three goals in four outings, keeping clean sheets in wins over St Mirren and Livingston.
Avoiding defeat on Wednesday would put McInnes's side on the brink of securing a relegation playoff as a bare minimum, but that may not be the best tactic to adopt versus opponents who know that this is their best chance of a win over their concluding double-header.
Dundee United Scottish Premiership form:
W
W
W
L
L
L
Kilmarnock Scottish Premiership form:
L
L
W
L
W
L
Team News
Dundee United will be forced into at least one change after Aziz Behich was sent off for two yellow cards during the defeat at Livingston.
Kai Fotheringham appears most likely to be introduced as a direct replacement, while Dylan Levitt may be recalled in central midfield.
Kilmarnock also have suspension issues with David Watson having been dismissed versus St Johnstone at the weekend.
Brad Lyons and Alan Power are each likely to come into the centre of the park with Liam Donnelly going off injured during the same fixture.
Dundee United possible starting lineup:
Birighitti; Niskanen, Ayina, Mulgrew, McMann; Harkes, Levitt; Middleton, McGrath, Fotheringham; Macleod
Kilmarnock possible starting lineup:
Walker; Mayo, Wright, Dorsett; Armstrong, Lyons, Chambers, Power, McKenzie; Vassell, Doidge
We say: Dundee United 2-1 Kilmarnock
On the back of their losing streak, Dundee United are up against it to respond with a potentially season-decisive win. Nevertheless, we are backing the home side to rise to the occasion at Tannadice, setting up a thrilling scenario for the final day.