| 2. Ronde | 16.08.2008 | Reading FC | - | Plymouth Argyle | 2:0 | ||||
| 3. Ronde | 23.08.2008 | Plymouth Argyle | - | Swansea City | 0:1 | ||||
| 13. Ronde | 25.10.2008 | Plymouth Argyle | - | Ipswich Town | 1:3 |  |
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| 14. Ronde | 28.10.2008 | Sheffield Wednesday | - | Plymouth Argyle | 0:1 | |
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| 15. Ronde | 01.11.2008 | Sheffield United | - | Plymouth Argyle | 2:0 | ||||
| 24. Ronde | 20.12.2008 | Barnsley FC | - | Plymouth Argyle | 2:0 | ||||
| 25. Ronde | 26.12.2008 | Plymouth Argyle | - | Southampton FC | 2:0 | ||||
| 26. Ronde | 28.12.2008 | Cardiff City | - | Plymouth Argyle | 1:0 |  |
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| 30. Ronde | 31.01.2009 | Ipswich Town | - | Plymouth Argyle | 0:0 | |
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| 31. Ronde | 03.02.2009 | Preston North End | - | Plymouth Argyle | 1:1 |
Schotland