| 16. Round | 14/11/2009 | Gillingham FC | - | Oldham Athletic | 1:0 | ||||
| 17. Round | 21/11/2009 | Bristol Rovers | - | Gillingham FC | 2:1 | ||||
| 18. Round | 24/11/2009 | Gillingham FC | - | Yeovil Town | 1:0 |  |
|||
| 19. Round | 01/12/2009 | Leyton Orient | - | Gillingham FC | 3:1 | ||||
| 22. Round | 19/12/2009 | Gillingham FC | - | Stockport County | 3:1 |  |
|||
| 23. Round | 26/12/2009 | Gillingham FC | - | Brentford FC | 0:1 | ||||
| 27. Round | 16/01/2010 | Swindon Town | - | Gillingham FC | 3:1 |
England