| Groep E | 16.07.2019 | Greenock Morton FC | - | Dumbarton FC | 6:1 | ||||
| Groep E | 19.07.2019 | Motherwell FC | - | Greenock Morton FC | 4:0 | ||||
| Groep E | 23.07.2019 | Annan Athletic | - | Greenock Morton FC | 0:5 |  |
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| Groep E | 27.07.2019 | Greenock Morton FC | - | Queen Of The South | 4:3 d.p. | ||||
| Achtste finale | 17.08.2019 | Hibernian FC | - | Greenock Morton FC | 5:3 n.v. |
Schotland