| Brentford FC v Gillingham FC 28/03/2009 | View match | |
| Gillingham FC v Barnet FC 04/04/2009 | View match | |
| Wycombe Wanderers FC v Gillingham FC 11/04/2009 | View match | |
| Gillingham FC v Dagenham & Redbridge 13/04/2009 | View match | |
| Chesterfield FC v Gillingham FC 18/04/2009 | View match | |
| Gillingham FC v Bury FC 25/04/2009 | View match | |
| Rochdale FC v Gillingham FC 02/05/2009 | View match | |
| Rochdale FC v Gillingham FC 07/05/2009 | View match | |
| Gillingham FC v Rochdale FC 10/05/2009 | View match | |
| Gillingham FC v Shrewsbury Town FC 23/05/2009 | View match | |
| Crystal Palace FC v Gillingham FC 02/08/2009 | View match | |
| Gillingham FC v Swindon Town FC 08/08/2009 | View match |