Fraser Murray and Kyle Vassell were the scorers as Dunfermline lost 2-0 at home to Kilmarnock – though the former was lucky not to be sent off just before half-time.
Murray was substituted at half-time after a late challenge on Lewis McCann that left the Pars forward needing treatment.
With Albion Rovers still to play, Dunfermline can only reach eight points in Group F of the Viaplay Cup and will require other results to go their way if they are to progress.
Pre-match, manager James McPake confirmed that Matty Todd will be out for the foreseeable with an ankle injury following a scan.
They will get a full diagnosis on Monday, the Pars boss told BBC Scotland, adding that he was “gutted” for the player.
How Dunfermline will likely line up: pic.twitter.com/6UPRSaVjq3
— Craig Cairns (@craigcairns001) July 22, 2023
Rhys Breen was the other player to drop out as the hosts made two changes from the side that swept Annan aside in midweek.
Chris Hamilton made his first start of the season, following a two-match suspension, as did Andrew Tod.
Pars fall behind early
The Pars fell behind early on when Murray finished Corrie Ndaba’s cutback. It came via one of a few moments of slack play.
Danny Armstrong later shot wide of the far post and Murray came close with another effort that dipped over the bar.
Dunfermline improved as the break neared, Andrew Tod had a speculative chip comfortably saved by Killie keeper William Dennis and Hamilton headed just over.
Aaron Comrie gambled at the back post not long before half-time and was almost rewarded when the ball looped towards him, but the attention of Matty Kennedy was enough to put him off.
Murray lucky to escape red
Just before that, Murray was lucky not to see red after a late challenge on McCann – Hamilton was also carded following the minor rammy that followed.
Both Hamilton and Murray were replaced by their managers at the break.
Dunfermline were the better side in the second half and Tod was involved in a lot of it, after moving into the No 10 role behind McCann and Wighton.
He latched on to a through ball and looked like he’d curled it beyond Dennis until the keeper pushed the ball away.
McCann then held on to the ball too long during a counter-attack when he should have released his strike partner.
There was another flashpoint, and another booking for each side when McCann clashed with Robbie Deas late in the game.
Second-half substitute Vassell then put the game beyond Dunfermline with an emphatic near-post finish – confirming the Pars’ first home defeat over 90 minutes since their Championship play-off defeat to Queen’s Park in May last year.
Tod was replaced in the final minutes by Taylor Sutherland to a standing ovation from the home support.
Dunfermline lineup
Dunfermline (3-4-3): Mehmet; Fisher, Benedictus (Breen), Otoo; Comrie, Hamilton (Allan), Chalmers, Edwards; Tod (Sutherland), Wighton, McCann. Subs not used: Little, Fenton, Hoggan.
