Challenge Cup| ROUND | R1 | R2 | QF | SF | F |
| Season archive |
| Tuesday, 12 August 2008 | ||||||
| r2 | Cowdenbeath | 3-2 | Albion Rovers | |||
| 8 | McQuade | 30 | Barr | |||
| 54 | Gemmell | 75 | Martin | |||
| 89 | Fairbairn | |||||
| r2 | Raith Rovers | 1-2 | Ross County | |||
| 74 | Weir | 52 | Keddie | |||
| 54 | Keddie | |||||
| r2 | Partick Thistle | 4-2 | Peterhead | |||
| 52 | Donnelly | 23 | Gunn | |||
| 90 | Harkins | 90 | Kozminski | |||
| 90 | McKeown | |||||
| 90 | McKeown | |||||
| r2 | Livingston | 1-0 | Forfar Athletic | |||
| 51 | Griffiths | |||||
| r2 | Alloa Athletic | 0-2 | Clyde | |||
| 58 | Clarke | |||||
| 76 | Gibson | |||||
| Wednesday, 13 August 2008 | ||||||
| r2 | East Stirlingshire | 0-3 | Morton | |||
| 22 | Masterton | |||||
| 32 | McGuffie | |||||
| 53 | McGuffie | |||||
| r2 | East Fife | 0-2 | Airdrieonians | |||
| 10 | Lynch | |||||
| 84 | Smith | |||||
| Wednesday, 20 August 2008 | ||||||
| r2 | Dunfermline | 0-2 | Queen of the South | |||
| 3 | Kean | |||||
| 75 | O'Connor | |||||
| 4 | +1 | Craig GUNN (Peterhead, 1p) |
| 3 | +1 | Stewart KEAN (Queen of the South) |
| +1 | Sean O'CONNOR (Queen of the South) | |
| +1 | Leigh GRIFFITHS (Livingston) | |
| 2 | +1 | Paul McQUADE (Cowdenbeath) |
| Alan TROUTEN (Clyde, 1p) | ||
| Martin BAVIDGE (Peterhead) | ||
| +2 | Ryan McGUFFIE (Morton) | |
| +2 | Stephen McKEOWN (Partick Thistle) | |
| +2 | Alex KEDDIE (Ross County) |
