Having failed to win any of the last seven meetings between the two sides, the Honest Men will head into the weekend looking to get one over the hosts and secure a second consecutive group victory.
Match preview
Dundee United got their League Cup campaign back on track as they picked up a dominant 3-0 victory over Stenhousemuir when the sides squared off at Tannadice on Tuesday.
Louis Moult and Declan Gallagher scored in an 11-minute spell to put the hosts in a commanding lead heading into the half-time break before Kristijan Trapanovski put the result beyond doubt with a 47th-minute strike.
This was a reaction that head coach Jim Goodwin would have wanted from his side after they suffered a somewhat disappointing 2-0 defeat at the hands of Falkirk FC in their cup opener on July 13.
Dundee United will now look to continue from where they left off last Tuesday as they look to close out the League Cup group stages on a high and gather momentum ahead of their return to the Premiership.
The Tangerines enjoyed a remarkable 2023-24 campaign as they picked up 23 wins and nine draws from their 36 games in the Championship to collect 75 points and clinch top spot, confirming their return to the top flight one year after going down.
Dundee United head into Saturday's clash on a run of four consecutive home victories and are unbeaten in each of their last six games at Tannadice, claiming five wins and one draw since February's 2-0 loss against Airdrieonians.
Ayr United, on the other hand, kicked off their quest for a first-ever League Cup title on Tuesday when they picked up a hard-earned 1-0 victory over Falkirk at Somerset Park.
After taking the load courtesy of Anton Dowds's fifth-minute effort, the Honest Men turned in a defensive show of class as they repelled John McGlynn's side to see out all three points.
This was in keeping with their strong display in pre-season, where Ayr went unbeaten in each of their four warm-up friendly matches, picking up three wins and one draw while scoring 12 goals and seven.
Scott Brown's men head into the new season off the back of a forgettable 2023-24 Championship campaign as they picked up just 44 points from 36 games to finish seventh in the table, just three points above the relegation zone.
While Ayr will be looking to build on Tuesday's result and make it two consecutive wins to start the season, they face the stern challenge of taking on an opposing side who have won each of their most recent five meetings and are unbeaten 12 of the last 16 encounters since August 2016.
Dundee United Scottish League Cup form:
L
W
Dundee United form (all competitions):
Ayr United Scottish League Cup form:
W
Ayr United form (all competitions):
Team News
Off the back of a dominant display against Stenhousemuir, Goodwin could name a similar starting XI this weekend, with Gallagher, Vicko Sevelj and Ross Graham teaming up at the defensive end of the pitch.
Experienced goalkeeper Dave Richards, who recently completed a move from St Johnstone, made his debut against Stenhousemuir on Tuesday and the 30-year-old should retain his role between the sticks.
Moult, who finished with 18 goals and 16 assists in the Championship last season, should spearhead the Tangerines' attack once again, alongside Trapanovski and Kai Fotheringham.
Having finished with 13 goals and five assists in the Championship last season, Dowds hit the ground running this term this season, netting in each of Ayr's four matches since pre-season, and the Scottish forward will be one to keep an eye on.
The Honest Men will take to the pitch without 27-year-old defender Nathan McGinley, who recently completed a move to England non-league side Spennymoor Town.
Ayr recently completed the signing of Mikey Devlin from Livingston and the 30-year-old defender could be handed his debut this weekend.
Dundee United possible starting lineup:
Richards; Gallagher, Sevelj, Graham; Strain, Sibbald, Babunski, Ferry; Trapanovski, Moult, Fotheringham
Ayr United possible starting lineup:
Stone; Watret, Stanger, McMann, Reading; Syla, McKenzie; Henderson, Oakley, Rus; Dowds
We say: Dundee United 2-1 Ayr United
With their quest of progressing from the group potentially resting on Saturday's results, we expect Dundee and Ayr United to take the game to each other in search of all three points. The Tangerines' home advantage gives them a slight edge here and we are tipping them to come away with the desired result.