Stephen O'Donnell netted an extra-time winner as Dundee overcame Arbroath in the first round of the Ramsdens Cup.
Arbroath's Gavin Swankie hit the crossbar before home keeper Darren Hill made great saves to deny Steven Milne and two efforts from Jamie McCluskey.
Jordan Elfverson headed Arbroath into a 77th-minute lead but Milne nodded in an equaliser moments later.
O'Donnell grabbed the decisive goal two minutes into extra-time, meeting Ryan Conroy's corner with a header.
Arbroath: Hill, Baxter, McAnespie, Malcolm, Busch, Falkingham (Jordan Elfverson 73), Bryce (Gibson 67), Kerr (Sibanda 109), Sheerin, Doris, Swankie. Subs Not Used: White, Wedderburn.
Booked: Sheerin, Malcolm, Sibanda.
Goals: Jordan Elfverson 77.
Dundee: Douglas, Irvine, Lockwood, Benedictis (McKeown 109), Weston, McCluskey, O'Donnell, Chisholm, Conroy, Hyde (Mcintosh 71), Milne. Subs Not Used: Gibson, McGregor, Ried.
Goals: Milne 79, O'Donnell 92.
Ref: Craig Charleston