Meeting in the Scottish League Cup round of 16, Kilmarnock and Ayr United go head to head at Rugby Park on Friday evening.
Both sides have been in league action since their last League Cup outings, with Kilmarnock suffering a heavy 5-1 defeat to Celtic in the Scottish Premiership, while Gary Naysmith's side continued their unbeaten start to the Scottish Championship season with a 1-1 draw away to Dunfermline on Saturday.
Match preview
Following a narrow escape from relegation last season, Kilmarnock endured a turbulent 2025-26 campaign that saw several changes in the dugout, with Stuart Kettlewell leaving his role after just seven months in charge while the side sat second bottom of the Scottish Premiership.
In early January, Kilmarnock turned to Neil McCann, who was tasked with keeping the East Ayrshire side in the top flight.
Although they made a shaky start under him, winning just once during his first month in charge, Killie eventually found some consistency and moved away from the relegation zone and ended the season with fourth straight wins.
While it was still a drop-off from previous years, with Kilmarnock having played in European qualifying two seasons ago, they stayed up with a six-point cushion over the bottom two and could now look ahead to their first full campaign with McCann at the helm.
They started the new season with Scottish League Cup action, winning three of their four matches to top Group H, although only two of those victories came in normal time, with one win and one defeat coming via penalty shootouts.
Kilmarnock therefore entered the knockout phase as the lowest-scoring group winners in the Scottish League Cup and have struggled since returning to Scottish Premiership action, losing both league games and conceding nine goals.
As for Ayr United, they arrive at the knockout stage of the Scottish League Cup with considerably more momentum behind them after making a strong start to life under Naysmith.
The Honest Men won all four of their group matches, scoring 10 goals and conceding just three, before ending the group stage with an emphatic 4-1 victory over Alloa.
Ayr finished the 2025-26 Scottish Championship season just three points above the relegation zone, having lost four of their final five matches, with their stronger form earlier in the campaign ultimately keeping them clear of danger.
One of the biggest problems during that inconsistent campaign was their inability to turn draws into victories, with Ayr's 15 stalemates the highest tally in the division, while no side recorded fewer than their eight wins.
The southwest Scotland side have started the new campaign in much better fashion, breezing through the Scottish League Cup before opening their Scottish Championship campaign with a win over Arbroath and a draw away to Dunfermline.
Wednesday's clash will be the eighth competitive meeting between the two sides, with their most recent encounter coming in 2022 when Kilmarnock ran out 3-1 winners.
Kilmarnock Scottish League Cup form:
Kilmarnock form (all competitions):
Ayr United Scottish League Cup form:
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Ayr United form (all competitions):
Team News
Following a heavy 5-1 defeat at Celtic Park last weekend, McCann may be tempted to make changes as Kilmarnock look to return to winning ways.
Michael Schjonning-Larsen scored in that defeat but was forced off with an injury soon afterwards, he is expected to miss out against Ayr United.
Mark O'Hara is the most likely candidate to come into the side at left-back in his absence.
Tyreece John-Jules was withdrawn during the 4-3 defeat to St Johnstone but returned to face Celtic and is expected to retain his place in attack alongside former Manchester United striker Joe Hugill.
As for the visitors, Ayr United will be keen to maintain their strong start to the campaign and could name an unchanged XI after reporting no fresh injury concerns following their latest match.
Owen Stirton is Ayr's leading scorer with three goals so far this season and is expected to lead the line once again.
Kilmarnock possible starting lineup:
Stryjek; Brandon, Stanger, Yfeko, O'Hara; Ring, Tshibola, Kiltie, Lowery; John-Jules, Hugill
Ayr United possible starting lineup:
Stone; Watret, McBeth, Holt, Dick; Lyon, Summers; Taylor, McKenzie, Mitchell; Stirton
We say: Kilmarnock 2-1 Ayr United
Although Ayr United arrive in the better form, Kilmarnock have the advantage of playing in the Scottish Premiership and we expect that difference in quality to prove decisive.
Ayr should make this a competitive and closely fought contest, but Kilmarnock's greater experience at this level could see them edge a cagey encounter and secure their first win in three matches.
For data analysis of the most likely results, scorelines and more for this match please click here.