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