| ROUND | R1 | R2 | R3 | QF | SF | F |
| Season archive |
| Tuesday, 5 August 2008 | ||||||
| r1 | Peterhead | 0-2 | Dunfermline | |||
| 46 | Phinn | |||||
| 50 | Kirk | |||||
| r1 | Stenhousemuir | 1-5 | St.Johnstone | |||
| 12 | Love | 23(p) | Sheerin | |||
| 78 | Milne | |||||
| 79 | Holmes | |||||
| 83 | Holmes | |||||
| 88 | Hardie | |||||
| r1 | Albion Rovers | 0-0 | Raith Rovers | aet, p3-4 | ||
| r1 | Dumbarton | 1-1 | Annan Athletic | aet, p5-4 | ||
| 115 | Logan | 103(p) | Jack | |||
| r1 | Montrose | 0-2 | Cowdenbeath | |||
| 6 | McGregor | |||||
| 81 | Fairbairn | |||||
| r1 | Partick Thistle | 4-3 | Forfar Athletic | aet | ||
| 39 | McKeown | 13 | Fotheringham | |||
| 70 | Gray | 65 | Lilley | |||
| 97 | Gray | 103 | Smith | |||
| 112 | Chaplain | |||||
| r1 | Ross County | 2-3 | Airdrieonians | aet | ||
| 43 | Daal | 23 | Di Giacomo | |||
| 76 | Hart | 86 | Noble | |||
| 112 | Di Giacomo | |||||
| r1 | Clyde | 4-1 | Queen's Park | |||
| 15 | MacLennan | 82 | Harkins | |||
| 63 | Gibson | |||||
| 86 | McSwegan | |||||
| 88 | McSwegan | |||||
| r1 | Stranraer | 3-6 | Morton | |||
| 37 | Frizzel | 5 | McGuffie | |||
| 72 | McColm | 12 | Wake | |||
| 84 | Gibson | 23 | Russell | |||
| 32 | Russell | |||||
| 40 | Paartalu | |||||
| 85 | Wake | |||||
| r1 | Alloa Athletic | 2-0 | Elgin City | |||
| 71 | Scott | |||||
| 78 | Kelly | |||||
| Wednesday, 6 August 2008 | ||||||
| r1 | Arbroath | 3-2 | Stirling Albion | |||
| 48 | McMullan | 5 | Graham | |||
| 64 | Wright | 63 | Harty | |||
| 80 | Bishop | |||||
| r1 | Ayr United | 2-1 | Berwick Rangers | |||
| 40 | Aitken | 12 | Greenhill | |||
| 45 | Williams | |||||
| r1 | East Fife | 0-3 | Brechin City | |||
| 44 | Twigg | |||||
| 65 | White | |||||
| 74 | Ward | |||||
| r1 | East Stirlingshire | 1-2 | Livingston | |||
| 90 | Graham | 80 | Fox | |||
| 90 | Smith | |||||
| 2 | +2 | Iain RUSSELL (Morton) |
| +2 | Paul DI GIACOMO (Airdrieonians) | |
| +2 | Damon GRAY (Partick Thistle) | |
| +2 | Brian WAKE (Morton) | |
| +2 | Derek HOLMES (St.Johnstone) | |
| +2 | Gary McSWEGAN (Clyde) |