 |
 |
|
| 12/07/2019 | 19:45 | Heart of Midlothian | - | Dundee United | 5:3 (1:1, 1:1) pso | |
| 13/07/2019 | 15:00 | Cowdenbeath FC | - | East Fife FC | 2:0 (2:0) | |
| 16/07/2019 | 19:30 | Stenhousemuir FC | - | Dundee United | 1:2 (0:0) | |
| 19:45 | Cowdenbeath FC | - | Heart of Midlothian | 0:2 (0:2) | ||
| 19/07/2019 | 19:45 | Dundee United | - | Cowdenbeath FC | 3:0 (1:0) | |
| 20/07/2019 | 15:00 | East Fife FC | - | Stenhousemuir FC | 2:0 (0:0) | |
| 23/07/2019 | 19:45 | Dundee United | - | East Fife FC | 0:2 (0:1) | |
| 24/07/2019 | 19:45 | Heart of Midlothian | - | Stenhousemuir FC | 2:1 (0:0) | |
| 27/07/2019 | 15:00 | East Fife FC | - | Heart of Midlothian | 7:6 (0:1, 1:1) pso | |
| 15:00 | Stenhousemuir FC | - | Cowdenbeath FC | 2:0 (1:0) |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Heart of Midlothian | 4 | 3 | 0 | 1 | 6:3 | 3 | 9 |
| 2 |
|
East Fife FC | 4 | 3 | 0 | 1 | 5:3 | 2 | 8 |
| 3 |
|
Dundee United | 4 | 2 | 0 | 2 | 6:4 | 2 | 7 |
| 4 |
|
Stenhousemuir FC | 4 | 1 | 0 | 3 | 4:6 | -2 | 3 |
| 5 |
|
Cowdenbeath FC | 4 | 1 | 0 | 3 | 2:7 | -5 | 3 |
| Next Round | |
