Ten-man Montrose upset local rivals Arbroath 1-0 to book their place in the second round of the Scottish Communities League Cup.
Ross McCord was the second-half match-winner for the League Two side against their League One hosts, who spurned a last-gasp penalty through Robert Linn.
Arbroath showed their intention early on, Alan Cook seeing his right-footed free-kick strike the crossbar, but it remained goalless at the break.
The visitors were then reduced to 10 men when Paul Watson was shown red for a foul on Ross Chisholm, but McCord duly fired home a spectacular 25-yard effort as the game entered the closing stages.
Montrose goalkeeper Stuart McKenzie preserved the precious advantage when he dived to keep out Linn's late spot-kick after Colin Hamilton was brought down.