| Dagenham & Redbridge v Gillingham FC 26/12/2008 | View match | |
| Gillingham FC v Wycombe Wanderers FC 28/12/2008 | View match | |
| Gillingham FC v Aston Villa FC 04/01/2009 | £5.90 | |
| Morecambe FC v Gillingham FC 17/01/2009 | View match | |
| Port Vale FC v Gillingham FC 20/01/2009 | View match | |
| Gillingham FC v Exeter City FC 24/01/2009 | View match | |
| Gillingham FC v Lincoln City FC 27/01/2009 | View match | |
| Gillingham FC v Bradford City FC 07/02/2009 | View match | |
| Rotherham United FC v Gillingham FC 14/02/2009 | View match | |
| Gillingham FC v Aldershot Town F.C 17/02/2009 | View match | |
| Gillingham FC v Macclesfield Town FC 21/02/2009 | View match | |
| Gillingham FC v AFC Bournemouth 28/02/2009 | View match |