Second Division Alloa Athletic paid for Scott Buist's sending off as they crashed out the Challenge Cup at the hands of Arbroath.
The defender was shown a straight red card after pulling back Barry Sellars when the Third Division side's captain was through on goal after 39 minutes.
Paul Watson took the resulting free-kick and Stuart McKay added a deft flick to send the keeper the wrong way.
Substitute Andy Reilly fired home from a Kevin Webster cross after 81 minutes.
Arbroath: Whight, McMullen (Rennie 54), Black, Campbell, Bishop, Watson, Webster, Hegarty (Reilly 75), Effem (Scott 57), Sellars, Stuart McKay.
Subs Not Used: Urjhert, Currie.
Booked: Black, Stuart McKay.
Goals: Stuart McKay 40, Reilly 81.
Alloa: Creer, McDougall, Fleming, Buist , Townsley, McKeown, Fairbairn (Wilson 60), Brown Ferguson, Brown (Mackie 74), Agnew (Kelly 58), Andrew.
Subs Not Used: Mark Ferguson, Jellema.
Sent Off: Buist (39). Booked: Townsley.
Ref: E Smith