| ROUND | R2 | R3 | R4 | R5 | R6 | QF | SF | F | |||
| r2 | R | r3 | R | r5 | R | ||||||
| Season archive |
| Saturday, 25 October 2008 | ||||||
| r2 | Berwick Rangers | 1-2 | Albion Rovers | |||
| r2 | Cove Rangers | 1-0 | Whitehill Welfare | |||
| r2 | Dalbeattie Star | 6-0 | Selkirk | |||
| r2 | Edinburgh City | 0-0 | Wick Academy | |||
| r2 | Forres Mechanics | 1-1 | Keith | |||
| r2 | Clachnacuddin | 1-0 | Crichton | |||
| r2 | Inverurie Locos | 5-1 | Banks o'Dee | |||
| r2 | Cowdenbeath | 1-2 | Elgin City | |||
| r2 | Fraserburgh | 0-1 | Dumbarton | |||
| r2 | Montrose | 2-0 | Huntly | |||
| r2 | Stenhousemuir | 5-0 | Threave Rovers | |||
| r2 | Lochee United | 3-0 | Buckie Thistle | |||
| r2 | Brora Rangers | 1-3 | Forfar Athletic | |||
| Sunday, 26 October 2008 | ||||||
| r2 | East Stirlingshire | 4-2 | Preston Athletic | |||
| Saturday, 1 November 2008 | ||||||
| r2 | Annan Athletic | 1-2 | Spartans | |||
| r2 | Civil Service Strollers | 0-1 | Vale of Leithen | |||
| r2R | Wick Academy | 1-4 | Edinburgh City | |||
| r2R | Keith | 1-1 | Forres Mechanics | aet, p0-3 | ||
| 2 | +2 | Andy SHIRRA (Stenhousemuir) |
| 1 | +1 | Ross CAMPBELL (Forfar Athletic) |
| +1 | Ross HARRIS (Albion Rovers) | |
| +1 | Kevin GORDON (Forfar Athletic) | |
| +1 | Darren GRIBBEN (Berwick Rangers) | |
| +1 | Calum SMITH (Montrose) | |
| +1 | Hugh DAVIDSON (Montrose) | |
| +1 | Paul McQUADE (Cowdenbeath) | |
| +1 | David DUNN (Forfar Athletic) | |
| +1 | Kenny WRIGHT (Elgin City) | |
| +1 | Colin CRAMB (East Stirlingshire) | |
| +1 | Brian GRAHAM (East Stirlingshire) | |
| +1 | Andy RODGERS (East Stirlingshire, 1p) | |
| +1 | Kevin NEILSON (Annan Athletic) | |
| +1 | Iain CHISHOLM (Dumbarton) | |
| +1 | Tommy COYNE (Albion Rovers) | |
| +1 | Gary THOM (Stenhousemuir) | |
| +1 | Paul KACZAN (Elgin City) | |
| +1 | Iain THOMSON (Stenhousemuir) | |
| +1 | Kevin MOTION (Stenhousemuir) | |
| +1 | Sean ANDERSON (East Stirlingshire) |