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| 11/10/2019 | 19:35 | Stenhousemuir FC | - | Waterford FC | 3:2 (1:1) | |
| 12/10/2019 | 15:00 | Arbroath FC | - | Clyde FC | 0:2 (0:1) | |
| 15:00 | Airdrieonians FC | - | Elgin City | 0:2 (0:0) | ||
| 15:00 | Raith Rovers | - | Glenavon FC | 3:1 (2:1) | ||
| 15:00 | Wrexham AFC | - | St. Mirren FC (R) | 4:1 (0:0) | ||
| 15:00 | Inverness CT | - | Alloa Athletic | 3:0 (1:0) | ||
| 17:15 | Partick Thistle | - | Connah's Quay Nomads | 2:0 (1:0) | ||
| 29/10/2019 | 19:45 | Solihull Moors | - | Rangers FC (R) | 3:4 (2:1, 3:3) pso |
