(AET - Cupar win 5-4 on penalities)
Cupar Hearts travelled to Glasgow to face last year’s Scottish Cup finalists Southside in a fourth round replay.
This was a cup tie that had everything from highs to lows, extra time, penalties and red cards.
The home side opened the scoring when a long throw by Gary Carroll found Chris Seenan whose overhead kick found the net.
Cupar got level with 51 minutes on the clock when Kyle Watson’s looping ball left Ryan Gray with an easy tap in to equalise.
Hearts took the lead when a Lee Sibanda free kick found Steven Pennington who played it wide for Ryan Gray to deliver and Sean Murdoch had time to compose himself in the box before firing the ball into the net.
But their lead didn’t last long though when Cupar conceded from a free kick that was headed in by Stephen Waddell.
The game went into extra time where only three minutes in an elbow saw Chris Seenan sent for an early bath.
Hearts soon found themselves with only 10 when a foul by Sean Murdoch saw the referee point to the spot and show him red. Stephen Waddell stepped up and netted before Cupar grabbed an equaliser to take the game to penalties thanks to Paul Laurie.
Both sides scored their first two penalties before Hearts missed their third and Southside their fourth and sudden death was needed.
Southside stepped up and missed their sixth leaving Scott McKay to send Hearts into the fifth round and he duly obliged.
On Saturday Cupar Hearts travel to face Shortlees in the fifth round of the Scottish Cup.
Cupar Hearts - Wilson, Anderson, Murdoch, K. Brown, Blyth, Wainwright, McKinnon, Gray, Pennington, Sibanda and Watson.
Subs - McInroy, McKay, Diop, Leadbetter, G. Brown and Laurie.