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| 29/08/2017 | 19:45 | Ayr United | - | Montrose FC | 5:6 (1:1, 1:1, 1:1) pso | |
| 01/09/2017 | 19:45 | Stranraer FC | - | Partick Thistle | 2:0 (1:0) | |
| 02/09/2017 | 14:30 | Dumbarton FC | - | Connah's Quay Nomads | 2:1 (0:1, 1:1) aet | |
| 15:00 | Crusaders FC | - | Motherwell FC (R) | 3:2 (1:0) | ||
| 15:00 | The Spartans FC | - | Linfield FC | 1:2 (0:1) | ||
| 15:00 | Peterhead FC | - | Annan Athletic | 2:0 (0:0) | ||
| 15:00 | Dundee United | - | Alloa Athletic | 3:1 (0:0) | ||
| 15:00 | Berwick Rangers | - | Queen Of The South | 0:5 (0:0) | ||
| 15:00 | St. Mirren FC | - | Heart of Midlothian (R) | 3:1 (1:0) | ||
| 15:00 | Hamilton Academical (R) | - | Cove Rangers | 1:3 (0:3) | ||
| 15:00 | Aberdeen FC (R) | - | Inverness CT | 2:4 (0:3) | ||
| 15:00 | Buckie Thistle | - | Dunfermline Athletic | 0:3 (0:3) | ||
| 15:00 | Raith Rovers | - | Ross County FC (R) | 4:0 (4:0) | ||
| 15:00 | Elgin City | - | Bray Wanderers | 2:0 (0:0) | ||
| 19:45 | Sligo Rovers | - | Falkirk FC | 1:2 (1:2) | ||
| 03/09/2017 | 14:45 | The New Saints | - | Livingston FC | 6:5 (1:0, 1:1, 1:1) pso |
