| Crystal Palace FC v Gillingham FC 02/08/2009 | View match | |
| Gillingham FC v Swindon Town FC 08/08/2009 | View match | |
| Gillingham FC v Plymouth Argyle FC 11/08/2009 | View match | |
| Tranmere Rovers FC v Gillingham FC 15/08/2009 | View match | |
| Colchester United FC v Gillingham FC 18/08/2009 | View match | |
| Gillingham FC v Hartlepool United 22/08/2009 | View match | |
| Gillingham FC v Blackburn Rovers FC 25/08/2009 | View match | |
| Walsall FC v Gillingham FC 29/08/2009 | View match | |
| Gillingham FC v Exeter City FC 05/09/2009 | View match | |
| Gillingham FC v Millwall FC 12/09/2009 | View match | |
| Leeds United FC v Gillingham FC 19/09/2009 | £4.80 | |
| Leeds United FC v Gillingham FC 19/09/2009 | £4.00 |