Group D | 13/07/2019 | Raith Rovers | - | Dundee FC | 0:3 | ||||
Group D | 17/07/2019 | Cove Rangers | - | Dundee FC | 2:3 pso | ||||
Group D | 20/07/2019 | Dundee FC | - | Peterhead FC | 4:2 pso | ||||
Group D | 28/07/2019 | Dundee FC | - | Inverness CT | 1:0 | ||||
Round of 16 | 18/08/2019 | Dundee FC | - | Aberdeen FC | 1:2 aet |