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| 03/09/2016 | 15:00 | Albion Rovers | - | St. Mirren FC | 3:4 (3:3, 3:3) aet | |
| 15:00 | Alloa Athletic | - | East Fife FC | 3:0 (3:0) | ||
| 15:00 | Brechin City FC | - | Dunfermline Athletic | 1:5 (1:2) | ||
| 15:00 | Dundee United | - | Peterhead FC | 3:2 (2:2, 2:2) aet | ||
| 15:00 | Falkirk FC | - | Elgin City | 6:1 (3:1) | ||
| 15:00 | Forfar Athletic | - | Raith Rovers | 3:2 (2:1) | ||
| 15:00 | Queen Of The South | - | Stenhousemuir FC | 7:1 (4:0) | ||
| 15:00 | Queen's Park FC | - | Greenock Morton FC | 2:0 (1:0) | ||
| 15:00 | Stranraer FC | - | Dumbarton FC | 1:0 (0:0) | ||
| 17:15 | Livingston FC | - | Celtic FC (R) | 5:1 (5:1) | ||
| 04/09/2016 | 15:00 | Ayr United | - | Airdrieonians FC | 3:2 (2:1, 2:2) aet | |
| 15:00 | Turriff United | - | Hibernian FC | 0:3 (0:2) |
