The Honest Men will be looking to cause an upset of their own this Saturday in order to continue in the competition.
Match preview
Tam Courts's team responded well from their opening day of the season defeat against Aberdeen by beating the defending Scottish Premiership champions Rangers in a shocking victory.
Dundee United defended well throughout the game to help end the dominant run of Gerrard's squad, earning their first three points of the campaign in the process.
Jamie Robson was the man to find the back of the net in the only goal of the game to earn the 1-0 victory, scoring for the first time since 2017 in order to make it happen.
The Terrors have plenty of confidence within them right now as their defeat to Aberdeen is the only game they have lost in their previous seven, which included an impressive set of group stage performances in the Scottish League Cup.
Courts's squad won all four of their group games, with a trio of 1-0 victories as well as an emphatic 6-1 win against Elgin City which all helped to get the team into this stage of the competition.
Dundee United will be hoping to go one step further than last season in the Scottish League Cup where they proved their quality by making it all the way to the semi-final, being knocked out by Hibernian.
On the other hand, Ayr United failed to progress past this round after being knocked out by Livingston in what proved to be a difficult campaign for the club.
Last season saw the Honest Men gain a new chairman, while former manager Mark Kerr also departed the club in February, with former Leeds United star David Hopkin taking charge from that point.
After finishing in eighth place in the 2020-21 Scottish Championship, the new campaign has also not begun with a perfect start for the squad due to a loss and a draw kicking things off.
The opening day saw a 2-0 loss away at Kilmarnock, but an 87th-minute strike from Mark McKenzie was enough to see Ayr United gain a point in a 2-2 draw against Arbroath in their first fixture at Somerset Park.
Ayr United Scottish League Cup form:
Ayr United form (all competitions):
Dundee United Scottish League Cup form:
Dundee United form (all competitions):
Team News
Dundee United sold Lawrence Shankland this week to Beerschot for £1m and because of that, the squad will be without the talented frontman who actually spent two years playing for Ayr earlier in his career.
He is not the only player that will be unavailable in the cup game though, with Mark Connolly still injured due to the cruciate ligament rupture he sustained back in May, while Declan Glass is still out of action due to a knee problem.
Unfortunately, during the victory against Rangers Logan Chalmers suffered a calf injury and had to be substituted off the pitch, with Adrian Sporle likely to slot into his position against Ayr.
Jeando Fuchs impressed throughout the game on Saturday after being brought in for his first start of the season, which could see him also retain his place in the starting lineup this weekend.
For the Honest Men, this game could prove to be an opportunity to give new signing Jonathan Afolabi a chance to start after joining the club on loan from Celtic.
Afolabi appeared from the bench against Arbroath, as did McKenzie who managed to get himself on the scoresheet, which could lead to him being given the opportunity to show what he is capable of from the first minute this time out.
Ayr United possible starting lineup:
Albinson; Fjortoft, Baird, McGinty; Houston, McKenzie, Murdoch, Maxwell, Reading; Afolabi, Adeloye
Dundee United possible starting lineup:
Siegrist; Smith, Edwards, Mulgrew, Robson; Harkes, Butcher, Fuchs; Sporle, Pawlett, Clark
We say: Ayr United 0-2 Dundee United
Coming into the game as the clear favourites will no doubt help Dundee United and with the confidence from defeating Rangers last week, there will be plenty of belief running through the squad.
The Terrors do have a slight advantage in terms of quality which is to be expected by being one division higher and that should be enough to see them into the next round.