Cupar Hearts lost out to the odd goal in five when they turned their attention back to the Kingdom Caledonian League to face Bowhill Rovers.
Hearts twice came from behind only to be dealt a devastating blow when they gambled and left space at the back for Jamie Leslie to fire in a 90th minute winner.
The home side opened the scoring when Leslie blasted in from close range.
Their lead didn’t last long and Lee Sibanda netted from the spot before Bowhill went ahead through Sami Mitchell.
Cupar grabbed the equaliser when Sibanda twisted and turned before finally hitting the net.
The home side were reduced to 10 men just before the break when Scott Eastaugh chopped down Sibanda and picked up a second yellow.
A free kick by Grant Blyth pushed Hearts forward in the remaining seconds but his strike was turned around the post for a corner.
Bowhill cleared and were quick to break with Leslie left unmarked to slot home.
Tomorrow (Saturday) Cupar Hearts travel to face Strathmiglo United in the first round of the Fife Cup.
Cupar Hearts - Inglis, Anderson, Blyth, McInroy, McLuckie, Brown (c), Wainwright, Gray, Dow, Dobes and Sibanda.
Subs - Leadbetter, Watson, Sutherland, McGuire, Calcutt.