| 5. Round | 13/09/2008 | Plymouth Argyle | - | Norwich City | 1:2 | ||||
| 6. Round | 16/09/2008 | Watford FC | - | Plymouth Argyle | 1:2 | ||||
| 7. Round | 20/09/2008 | Crystal Palace | - | Plymouth Argyle | 1:2 | ||||
| 8. Round | 27/09/2008 | Plymouth Argyle | - | Nottingham Forest | 1:0 | ||||
| 9. Round | 30/09/2008 | Bristol City | - | Plymouth Argyle | 2:2 | ||||
| 18. Round | 22/11/2008 | Plymouth Argyle | - | Cardiff City | 2:1 | ||||
| 19. Round | 25/11/2008 | Southampton FC | - | Plymouth Argyle | 0:0 | ||||
| 20. Round | 29/11/2008 | Plymouth Argyle | - | Blackpool FC | 1:2 | ||||
| 21. Round | 06/12/2008 | Doncaster Rovers | - | Plymouth Argyle | 1:0 | ||||
| 26. Round | 28/12/2008 | Cardiff City | - | Plymouth Argyle | 1:0 | ||||
| 28. Round | 17/01/2009 | Nottingham Forest | - | Plymouth Argyle | 2:0 |
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