22nd September 2016
| 3rd Round | Aberdeen | 0-0 | St. Johnstone |
21st September 2016
| 3rd Round | Celtic | 0-0 | Alloa Athletic |
20th September 2016
| 3rd Round | Rangers | 0-0 | Queen of the South |
| 3rd Round | Greenock Morton | 0-0 | Dundee United |
10th August 2016
| 2nd Round | Ayr United | 1-2 | Aberdeen |
| 2nd Round | Celtic | 5-0 | Motherwell |
| 2nd Round | St. Johnstone | 3-2 | Heart of Midlothian |
9th August 2016
| 2nd Round | Rangers | 5-0 | Peterhead |
| 2nd Round | Hibernian | 1-3 | Queen of the South |
| 2nd Round | 1-2 | Greenock Morton |
| 2nd Round | Dundee United | 3-1 | Partick Thistle |
| 2nd Round | Alloa Athletic | 1-0 | Inverness Caledonian Thistle |
31st July 2016
| Inverness Caledonian Thistle | 7-0 | Arbroath |
| Dundee United | 2-0 | Dunfermline Athletic |
30th July 2016
| Kilmarnock | 0-0 | Albion Rovers |
| St. Mirren | 3-0 | Edinburgh City |
| 2-1 |
| Stranraer | 0-3 | Motherwell |
| 0-2 | Annan Athletic |
| Queen of the South | 1-0 | Stenhousemuir |
| Partick Thistle | 2-0 | Queen's Park |
| Ross County | 7-0 | Cove Rangers |
| Raith Rovers | 0-1 | Alloa Athletic |
| St. Johnstone | 4-0 | Stirling Albion |
| Falkirk | 2-0 | Brechin City |
| Greenock Morton | 2-0 |
| Dumbarton | 3-3 | Peterhead |
| Dundee | 7-0 | Forfar Athletic |
27th July 2016
| Cove Rangers | 3-0 | Montrose |
| Edinburgh City | 2-4 |
| Arbroath | 0-2 | Cowdenbeath |
| Alloa Athletic | 3-2 | Ross County |
26th July 2016
| Peterhead | 2-1 | Dundee |
| 2-3 | Kilmarnock |
| Albion Rovers | 1-2 | Clyde |
| 0-2 | Ayr United |
| Motherwell | 3-0 |
| Dunfermline Athletic | 1-5 | Inverness Caledonian Thistle |
| Stirling Albion | 4-1 | Elgin City |
| Brechin City | 1-1 | St. Johnstone |
| Forfar Athletic | 2-0 | East Fife |
| Stenhousemuir | 1-4 | Partick Thistle |
| Queen's Park | 3-3 | Airdrie United |
25th July 2016
| Rangers | 3-0 | Stranraer |
23rd July 2016
| Ross County | 1-1 | Raith Rovers |
| Kilmarnock | 0-2 | Greenock Morton |
| Clyde | 1-1 |
| Dundee | 6-2 | Dumbarton |
| Cowdenbeath | 0-3 | Dunfermline Athletic |
| East Fife | 2-1 | Peterhead |
| Elgin City | 4-2 | Brechin City |
| St. Johnstone | 3-0 | Falkirk |
| Inverness Caledonian Thistle | 1-1 | Dundee United |
| Montrose | 0-2 | Alloa Athletic |
| Airdrie United | 2-1 | Stenhousemuir |
| Partick Thistle | 2-1 | Queen of the South |
| Annan Athletic | 1-3 | Motherwell |
| Ayr United | 1-0 | Edinburgh City |
| 3-0 | St. Mirren |
22nd July 2016
| 0-3 | Rangers |
20th July 2016
| Edinburgh City | 0-3 |
19th July 2016
| Stenhousemuir | 0-2 | Queen's Park |
| Alloa Athletic | 4-0 | Cove Rangers |
| Peterhead | 2-0 | Forfar Athletic |
| Greenock Morton | 1-0 | Clyde |
| 0-0 | Albion Rovers |
| St. Mirren | 1-0 | Ayr United |
| Stranraer | 3-1 |
| Rangers | 2-0 | Annan Athletic |
| Queen of the South | 2-0 | Airdrie United |
| Raith Rovers | 2-1 | Montrose |
| Dunfermline Athletic | 3-0 | Arbroath |
| Dundee United | 6-1 | Cowdenbeath |
| Falkirk | 3-0 | Elgin City |
| Brechin City | 2-1 | Stirling Albion |
| Dumbarton | 0-2 | East Fife |
16th July 2016
| 2-3 | St. Mirren |
| Ayr United | 2-1 |
| Motherwell | 0-2 | Rangers |
| Annan Athletic | 1-2 | Stranraer |
| East Fife | 1-1 | Dundee |
| Clyde | 1-2 | Kilmarnock |
| Montrose | 0-1 | Ross County |
| Cowdenbeath | 1-2 | Inverness Caledonian Thistle |
| Stirling Albion | 1-0 | Falkirk |
| Elgin City | 1-3 | St. Johnstone |
| Forfar Athletic | 2-2 | Dumbarton |
| Albion Rovers | 0-0 | Greenock Morton |
| Queen's Park | 0-2 | Queen of the South |
15th July 2016
| Cove Rangers | 1-2 | Raith Rovers |
| Arbroath | 1-1 | Dundee United |
| Airdrie United | 0-1 | Partick Thistle |