| 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 | |
| Notts County FC v Gillingham FC 17/03/2009 | View match | |
| Grimsby Town FC v Gillingham FC 21/03/2009 | View match | |
| 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 |