| Gillingham FC v Stockport County FC 29/11/2008 | View match | |
| Gillingham FC v Chesterfield FC 06/12/2008 | View match | |
| Stockport County FC v Gillingham FC 09/12/2008 | View match | |
| Barnet FC v Gillingham FC 13/12/2008 | View match | |
| Gillingham FC v Brentford FC 20/12/2008 | View match | |
| 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 |