| 2. Round | 15/08/2009 | Leyton Orient | - | Oldham Athletic | 1:2 | ||||
| 7. Round | 12/09/2009 | Bristol Rovers | - | Oldham Athletic | 1:0 | ||||
| 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 | ||||
| 11. Round | 03/10/2009 | Oldham Athletic | - | Yeovil Town | 0:0 | ||||
| 12. Round | 10/10/2009 | Charlton Athletic | - | Oldham Athletic | 0:0 |  |
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| 13. Round | 17/10/2009 | Oldham Athletic | - | Southampton FC | 1:3 | |
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| 14. Round | 24/10/2009 | Brighton & Hove Albion | - | Oldham Athletic | 0:2 | ||||
| 18. Round | 24/11/2009 | Walsall FC | - | Oldham Athletic | 3:0 | ||||
| 19. Round | 01/12/2009 | Oldham Athletic | - | Leeds United | 0:2 | ||||
| 20. Round | 05/12/2009 | Norwich City | - | Oldham Athletic | 2:0 | ||||
| 21. Round | 12/12/2009 | Oldham Athletic | - | Exeter City | 2:0 | ||||
| 33. Round | 23/02/2010 | Leeds United | - | Oldham Athletic | 2:0 | ||||
| 29. Round | 30/03/2010 | Oldham Athletic | - | Brentford FC | 2:3 |
England