| ROUND | R1 | R2 | R3 | QF | SF | F |
| Season archive |
| Tuesday, 23 September 2008 | ||||||
| r3 | Dunfermline | 2-0 | St.Mirren | |||
| 69 | Bayne | |||||
| 74 | Wiles | |||||
| r3 | Celtic | 4-0 | Livingston | |||
| 24 | Loovens | |||||
| 64 | Samaras | |||||
| 81 | Brown | |||||
| 85(p) | Samaras | |||||
| r3 | Falkirk | 2-1 | Queen of the South | |||
| 29 | McCann | 58 | Kean | |||
| 73 | Lovell | |||||
| r3 | Morton | 1-2 | Inverness CT | aet | ||
| 34 | McAlister | 79 | Hastings | |||
| 111 | Imrie | |||||
| r3 | Dundee United | 2-0 | Airdrieonians | |||
| 33 | Goodwillie | |||||
| 42 | Robertson | |||||
| Wednesday, 24 September 2008 | ||||||
| r3 | Kilmarnock | 4-2 | Aberdeen | |||
| 2 | Sammon | 6 | McDonald | |||
| 12 | David | 26(p) | Miller | |||
| 17(p) | Taouil | |||||
| 33 | Sammon | |||||
| r3 | Motherwell | 1-2 | Hamilton | |||
| 66 | Murphy | 53 | Graham | |||
| 90 | Ettien | |||||
| r3 | Partick Thistle | 1-2 | Rangers | aet | ||
| 33 | McKeown | 25 | Boyd | |||
| 116 | Pedro Mendes | |||||
| 4 | Iain RUSSELL (Morton, 1p) | |
| 3 | +1 | David GOODWILLIE (Dundee United) |
| Jon DALY (Dundee United) | ||
| Billy MEHMET (St.Mirren) | ||
| 2 | Paul DI GIACOMO (Airdrieonians) | |
| +2 | Georgios SAMARAS (Celtic, 1p) | |
| Damon GRAY (Partick Thistle) | ||
| Brian WAKE (Morton) | ||
| Andy KIRK (Dunfermline) | ||
| Derek HOLMES (St.Johnstone) | ||
| Gary McSWEGAN (Clyde) | ||
| +2 | Conor SAMMON (Kilmarnock) | |
| +1 | Stephen McKEOWN (Partick Thistle) |