These two sides met four times in the 2024/25 campaign. The first two meetings were won by the Saints. The first of which came at Rugby Park, where St Johnstone ran out 3-0 winners, courtesy of a brace from Sidibeh and a late penalty from Kimpioka. The second came in Perth, where St Johnstone won 1-0, with Kirk scoring the only goal of the game.

The other two meetings were both won by Kilmarnock. The first of which came in Ayrshire, where Killie ran out 3-1 winners, courtesy of goals from Polworth, Murray and Wales. Carey scored a consolation in stoppage time for the Saints. The second of which, and the final meeting between these two sides in the 24/25 campaign ended 2-0 to Kilmarnock in Perth. Watson and Armstrong got the goals.

Both sides had underwhelming League Cup group stage campaigns. Sunday’s hosts St Johnstone started off their campaign with a 2-0 win away at Linlithgow Rose, then followed that result up with a 3-0 win against Championship side Morton. However, defeat against Inverness Caledonian Thistle, followed up by a 1-1 draw against East Fife, in a game where they took the lead in the 90th minute and conceded in the 95th, then lost on penalties, meant they were knocked out of the competition.

Kilmarnock kicked off their campaign with a 0-0 draw against Raith Rovers, however, did pick up the extra point. In their second match of the group stage, Neil McCann’s side showed resilience to beat Elgin City 1-0. Killie were reduced to ten in the first-half when Brandon was shown red, but Hugill’s stoppage time winner prevented back-to-back penalty shootouts. Their third match ended in a 1-0 win against Hamilton Accies, courtesy of a strike from Kiltie on the hour mark. Kilmarnock rounded off their group stage campaign with yet another poor showing, losing to League One outfit Peterhead on penalties after another goalless draw. Despite a disappointing group campaign, where they only netted twice, Killie finished top of their group on nine points, and will face Ayrshire rivals Ayr United in the next round.

Both sides have been active in the transfer market. The Saints have brought in some familiar faces, including Ruari Paton and Toby Steward, who were part of the St Johnstone squad that won the Championship last season. In continuation, the Perth side have brought in two players who had brilliant campaigns last season in the Scottish Championship – Chalmers from Partick Thistle and Matty Todd from Dunfermline Athletic.

Kilmarnock have brought in a mix of youth and experience. Mark O’Hara signed in late June, returning to the club where it all started for him back in 2012. Tshibola also made his return to Rugby Park following the World Cup, where he was part of the DR Congo squad. Killie have also brought in young Rangers midfielder Bailey Rice, who will be looking to emulate the success that Findlay Curtis had during his loan spell at Rugby Park, during the second-half of last season, and young Welsh forward Ieuan Owen, who scored two huge goals which helped Barry Town secure the club’s first top-flight silverware in over two decades.