1. Round | 03/08/2019 | Arbroath FC | - | Queen Of The South | 0:0 | ||||
6. Round | 21/09/2019 | Inverness CT | - | Queen Of The South | 2:0 | ||||
13. Round | 09/11/2019 | Queen Of The South | - | Ayr United | 3:1 | ||||
14. Round | 16/11/2019 | Dundee United | - | Queen Of The South | 3:0 |