| 1. Round | 08/08/2009 | Gillingham FC | - | Swindon Town | 5:0 | ||||
| 14. Round | 24/10/2009 | Gillingham FC | - | Charlton Athletic | 1:1 | ||||
| 21. Round | 12/12/2009 | Huddersfield Town | - | Gillingham FC | 2:1 | ||||
| 22. Round | 19/12/2009 | Gillingham FC | - | Stockport County | 3:1 | ||||
| 24. Round | 28/12/2009 | Exeter City | - | Gillingham FC | 1:1 | ||||
| 27. Round | 16/01/2010 | Swindon Town | - | Gillingham FC | 3:1 | ||||
| 28. Round | 23/01/2010 | Gillingham FC | - | Colchester United | 0:0 | ||||
| 25. Round | 26/01/2010 | Hartlepool United | - | Gillingham FC | 1:1 |
England