| 21. Round | 10/12/2005 | Gillingham FC | - | Port Vale FC | 3:0 | ||||
| 25. Round | 31/12/2005 | Gillingham FC | - | Milton Keynes Dons | 3:0 | ||||
| 26. Round | 02/01/2006 | Huddersfield Town | - | Gillingham FC | 0:0 | ||||
| 27. Round | 10/01/2006 | Barnsley FC | - | Gillingham FC | 1:0 | ||||
| 28. Round | 14/01/2006 | Gillingham FC | - | Swindon Town | 3:0 | ||||
| 29. Round | 21/01/2006 | Oldham Athletic | - | Gillingham FC | 2:0 | ||||
| 30. Round | 28/01/2006 | Gillingham FC | - | Rotherham United | 1:1 |  |
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| 24. Round | 31/01/2006 | Swansea City | - | Gillingham FC | 1:2 | ||||
| 34. Round | 18/02/2006 | Doncaster Rovers | - | Gillingham FC | 2:0 | ||||
| 35. Round | 25/02/2006 | Gillingham FC | - | Scunthorpe United | 1:3 |
England