| ROUND | R1 | R2 | R3 | QF | SF | F |
| Season archive |
| Tuesday, 28 October 2008 | ||||||
| qf | Dundee United | 1-0 | Dunfermline | |||
| 16 | Robertson | |||||
| qf | Rangers | 2-0 | Hamilton | |||
| 25 | Boyd | |||||
| 50 | Lafferty | |||||
| qf | Falkirk | 1-0 | Inverness CT | |||
| 36 | McCann | |||||
| Wednesday, 29 October 2008 | ||||||
| qf | Kilmarnock | 1-3 | Celtic | |||
| 68 | Invincible | 11 | McDonald | |||
| 45 | Nakamura | |||||
| 71 | McGeady | |||||
| 4 | Iain RUSSELL (Morton, 1p) | |
| 3 | David GOODWILLIE (Dundee United) | |
| Jon DALY (Dundee United) | ||
| Billy MEHMET (St.Mirren) | ||
| 2 | Paul DI GIACOMO (Airdrieonians) | |
| Georgios SAMARAS (Celtic, 1p) | ||
| +1 | Scott ROBERTSON (Dundee United) | |
| +1 | Kris BOYD (Rangers) | |
| Damon GRAY (Partick Thistle) | ||
| Brian WAKE (Morton) | ||
| Andy KIRK (Dunfermline) | ||
| Derek HOLMES (St.Johnstone) | ||
| Gary McSWEGAN (Clyde) | ||
| Conor SAMMON (Kilmarnock) | ||
| Stephen McKEOWN (Partick Thistle) | ||
| +1 | Neil McCANN (Falkirk) |