| 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 | |
| Luton Town FC v Gillingham FC 03/03/2009 | £4.50 | |
| Accrington Stanley FC v Gillingham FC 07/03/2009 | View match | |
| Gillingham FC v Darlington FC 10/03/2009 | View match | |
| Gillingham FC v Shrewsbury Town FC 14/03/2009 | View match |