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| 06.09.2019 | 20:45 | Waterford FC | - | Heart of Midlothian (R) | 3:1 (1:0) | |
| 07.09.2019 | 14:00 | Airdrieonians FC | - | Bohemian FC | 3:2 (1:1) | |
| 16:00 | Stenhousemuir FC | - | The New Saints | 3:1 (0:0, 1:1) d.p. | ||
| 16:00 | Wrexham AFC | - | Ayr United | 6:5 (0:0, 1:1) d.p. | ||
| 16:00 | Kelty Hearts | - | Solihull Moors | 2:4 (1:0, 1:1) d.p. | ||
| 16:00 | Formartine United | - | Glenavon FC | 0:3 (0:1) | ||
| 16:00 | Inverness CT | - | Greenock Morton FC | 3:1 (2:0) | ||
| 16:00 | Montrose FC | - | Partick Thistle | 0:2 (0:1) | ||
| 16:00 | St. Mirren FC (R) | - | Stirling Albion FC | 1:0 (0:0) | ||
| 16:00 | Dundee United | - | Arbroath FC | 3:4 (0:0, 0:0) d.p. | ||
| 16:00 | Clyde FC | - | Queen Of The South | 3:2 (0:1) | ||
| 16:00 | Raith Rovers | - | Falkirk FC | 2:0 (1:0) | ||
| 16:00 | Dunfermline Athletic | - | Alloa Athletic | 1:2 (1:1) | ||
| 18:15 | Connah's Quay Nomads | - | Cove Rangers | 1:0 (0:0) | ||
| 08.09.2019 | 16:00 | Dundee FC | - | Elgin City | 1:2 (1:0) | |
| 18.09.2019 | 20:45 | Ballymena United | - | Rangers FC (R) | 0:1 (0:0) |
