16th November 2008
| Final | Airdrie United | 2-2 | Ross County |
12th October 2008
| Semi Final | Partick Thistle | 0-1 | Airdrie United |
| Semi Final | Ross County | 4-1 | Greenock Morton |
7th September 2008
| 3rd Round | Clyde | 0-1 | Ross County |
| 3rd Round | Cowdenbeath | 1-2 | Airdrie United |
| 3rd Round | Livingston | 0-2 | Partick Thistle |
| 3rd Round | Queen of the South | 0-2 | Greenock Morton |
20th August 2008
| 2nd Round | Dunfermline Athletic | 0-2 | Queen of the South |
13th August 2008
| 2nd Round | East Fife | 0-3 | Airdrie United |
| 2nd Round | 0-3 | Greenock Morton |
12th August 2008
| 2nd Round | Alloa Athletic | 0-2 | Clyde |
| 2nd Round | Cowdenbeath | 3-2 | Albion Rovers |
| 2nd Round | Livingston | 1-0 | Forfar Athletic |
| 2nd Round | Partick Thistle | 4-2 | Peterhead |
| 2nd Round | Raith Rovers | 1-2 | Ross County |
27th July 2008
| 1st Round South & West Region | 2-1 | Ayr United |
26th July 2008
| 1st Round South & West Region | Airdrie United | 3-2 | Dumbarton |
| 1st Round North & East Region | Alloa Athletic | 2-1 | Dundee |
| 1st Round North & East Region | Arbroath | 1-2 | Forfar Athletic |
| 1st Round South & West Region | 1-5 | Queen of the South |
| 1st Round North & East Region | Brechin City | 0-1 | East Fife |
| 1st Round South & West Region | Clyde | 2-0 | Annan Athletic |
| 1st Round North & East Region | Dunfermline Athletic | 3-0 | Stirling Albion |
| 1st Round North & East Region | Elgin City | 0-2 | Cowdenbeath |
| 1st Round South & West Region | Livingston | 4-0 | Stranraer |
| 1st Round South & West Region | Partick Thistle | 2-1 | Queen's Park |
| 1st Round North & East Region | Peterhead | 6-0 | Montrose |
| 1st Round North & East Region | Ross County | 2-1 | St. Johnstone |
| 1st Round South & West Region | Stenhousemuir | 0-1 | Albion Rovers |