Challenge Cup| ROUND | R1 | R2 | QF | SF | F |
| Season archive |
| Saturday, 26 July 2008 | ||||||
| r1 | Ross County | 2-1 | St.Johnstone | |||
| 53 | Winters | 84 | Samuel | |||
| 65 | Higgins | |||||
| r1 | Peterhead | 6-0 | Montrose | |||
| 24 | Bavidge | |||||
| 45(og) | Cumming | |||||
| 52 | Gunn | |||||
| 58 | Gunn | |||||
| 68(p) | Gunn | |||||
| 78 | Bavidge | |||||
| r1 | Alloa Athletic | 2-1 | Dundee | |||
| 59 | Townsley | 88 | Antoine-Curier | |||
| 83 | Stevenson | |||||
| r1 | Arbroath | 1-2 | Forfar Athletic | |||
| 44 | Scott | 62(p) | Kilgannon | |||
| 71(p) | McLeish | |||||
| r1 | Brechin City | 0-1 | East Fife | |||
| 69 | Templeman | |||||
| r1 | Dunfermline | 3-0 | Stirling Albion | |||
| 4 | Burke | |||||
| 61 | Phinn | |||||
| 74 | Williamson | |||||
| r1 | Elgin City | 0-2 | Cowdenbeath | |||
| 13 | McGregor | |||||
| 80 | McQuade | |||||
| r1 | Clyde | 2-0 | Annan Athletic | |||
| 61(p) | Trouten | |||||
| 74 | Trouten | |||||
| r1 | Stenhousemuir | 0-1 | Albion Rovers | |||
| 87(p) | Donnelly | |||||
| r1 | Partick Thistle | 2-1 | Queen's Park | |||
| 9 | Gray | 17 | Henry | |||
| 9 | Roberts | |||||
| r1 | Berwick Rangers | 1-5 | Queen of the South | |||
| 47 | Little | 12 | O'Connor | |||
| 31 | Kean | |||||
| 58 | O'Connor | |||||
| 65 | Kean | |||||
| 80 | Barr | |||||
| r1 | Livingston | 4-0 | Stranraer | |||
| 33 | Griffiths | |||||
| 67 | Hamill | |||||
| 70 | McParland | |||||
| 72 | Griffiths | |||||
| r1 | Airdrieonians | 3-2 | Dumbarton | |||
| 53 | Noble | 25 | Clark | |||
| 58 | Cardle | 43 | Carcary | |||
| 75 | Di Giacomo | |||||
| Sunday, 27 July 2008 | ||||||
| r1 | East Stirlingshire | 2-1 | Ayr United | |||
| 86 | Richardson | 15 | Williams | |||
| 89 | Rodgers | |||||
| 3 | +3 | Craig GUNN (Peterhead, 1p) |
| 2 | +2 | Stewart KEAN (Queen of the South) |
| +2 | Alan TROUTEN (Clyde, 1p) | |
| +2 | Martin BAVIDGE (Peterhead) | |
| +2 | Sean O'CONNOR (Queen of the South) | |
| +2 | Leigh GRIFFITHS (Livingston) |
