Stewart Kean missed a 90th-minute penalty as Arbroath beat Stenhousemuir in the Ramsdens Cup quarter-final.
Scott Robertson broke the deadlock when he headed home after Alex Keddie flicked on player-manager Paul Sheerin's corner.
And the visitors' task was made harder when John Gemmell was shown a straight red for a foul on Stuart Malcolm.
Stenny were handed a lifeline when Keddie upended Kean in the box only to blaze his spot-kick over.
Arbroath: Morrison, Baxter, Malcolm, Keddie, Hamilton, Rennie (Sibanda 74), Kerr, Scott Robertson (Birse 82), Sheerin, Holmes, Doris (Gribben 74). Subs Not Used: Gray, Travis.
Goals: Scott Robertson 34.
Stenhousemuir: Reidford, Ross, Buist (Rodgers 82), McMillan, Dickson, Ferguson (Craig Anderson 72), Hodge, Iain Thomson, Darren Smith, Gemmell, Kean. Subs Not Used: Shaw, Brash, O'Grady.
Sent Off: Gemmell (49).
Booked: Hodge,Rodgers,Iain Thomson.
Ref: Brian Colvin (Scotland).