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| 16.08.2016 | 20:30 | Partick Thistle (R) | - | Queen's Park FC | 5:6 (0:0, 1:1, 1:1) d.p. | |
| 20:45 | Brechin City FC | - | Cove Rangers | 4:1 (2:1) | ||
| 20:45 | Peterhead FC | - | Brora Rangers FC | 3:2 (0:1) | ||
| 20:45 | Elgin City | - | Heart of Midlothian (R) | 2:0 (1:0) | ||
| 20:45 | Aberdeen FC (R) | - | Forfar Athletic | 1:3 (0:1) | ||
| 20:45 | Stranraer FC | - | The Spartans FC | 7:1 (3:0) | ||
| 20:45 | Albion Rovers | - | Hamilton Academical (R) | 2:0 (1:0) | ||
| 20:45 | Motherwell FC (R) | - | Airdrieonians FC | 1:2 (0:1) | ||
| 20:45 | Cowdenbeath FC | - | Celtic FC (R) | 1:2 (1:0) | ||
| 17.08.2016 | 20:30 | Rangers FC (R) | - | Stenhousemuir FC | 1:3 (0:2) | |
| 20:45 | Arbroath FC | - | East Fife FC | 2:3 (1:0, 2:2) n.v. | ||
| 20:45 | Turriff United | - | Montrose FC | 1:0 (0:0) |
