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| 21/01/2017 | 12:30 | Rangers FC | - | Motherwell FC | 2:1 (0:0) | |
| 15:00 | Ross County FC | - | Dundee United | 6:2 (4:2) | ||
| 15:00 | St. Johnstone FC | - | Stenhousemuir FC | 2:0 (2:0) | ||
| 15:00 | Livingston FC | - | East Fife FC | 0:1 (0:1) | ||
| 15:00 | Aberdeen FC | - | Stranraer FC | 4:0 (2:0) | ||
| 15:00 | Elgin City | - | Inverness CT | 1:2 (1:1) | ||
| 15:00 | Kilmarnock FC | - | Hamilton Academical | 0:1 (0:0) | ||
| 15:00 | Bonnyrigg Rose Athletic | - | Hibernian FC | 1:8 (1:3) | ||
| 15:00 | Ayr United | - | Queen's Park FC | 0:0 (0:0) | ||
| 15:00 | Partick Thistle | - | Formartine United | 4:0 (3:0) | ||
| 15:00 | Stirling Albion FC | - | Clyde FC | 2:2 (1:1) | ||
| 15:00 | Alloa Athletic | - | Dunfermline Athletic | 2:3 (0:2) | ||
| 15:00 | Dundee FC | - | St. Mirren FC | 0:2 (0:1) | ||
| 15:00 | Greenock Morton FC | - | Falkirk FC | 2:0 (1:0) | ||
| 22/01/2017 | 13:05 | Raith Rovers | - | Heart of Midlothian | 1:1 (0:1) | |
| 15:00 | Albion Rovers | - | Celtic FC | 0:3 (0:1) | ||
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 24/01/2017 | 19:45 | Queen's Park FC | - | Ayr United | 4:5 (2:1, 2:2, 2:2) pso | |
| 25/01/2017 | 19:45 | Heart of Midlothian | - | Raith Rovers | 4:2 (1:1, 1:1) aet | |
| 31/01/2017 | 19:45 | Clyde FC | - | Stirling Albion FC | 3:2 (3:1) | |
