| 6. Round | 04/09/2009 | Oldham Athletic | - | Hartlepool United | 0:3 | ||||
| 7. Round | 12/09/2009 | Bristol Rovers | - | Oldham Athletic | 1:0 |  |
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| 8. Round | 19/09/2009 | Oldham Athletic | - | Carlisle United | 2:0 | ||||
| 9. Round | 26/09/2009 | Southend United | - | Oldham Athletic | 0:1 | ||||
| 10. Round | 29/09/2009 | Oldham Athletic | - | Milton Keynes Dons | 2:1 |  |
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| 11. Round | 03/10/2009 | Oldham Athletic | - | Yeovil Town | 0:0 | ||||
| 14. Round | 24/10/2009 | Brighton & Hove Albion | - | Oldham Athletic | 0:2 | ||||
| 15. Round | 01/11/2009 | Oldham Athletic | - | Huddersfield Town | 0:1 |
Ireland