| Gillingham FC v Wigan Athletic FC 12/08/1995 | View match | |
| Gillingham FC v Bristol Rovers FC 15/08/1995 | View match | |
| Lincoln City FC v Gillingham FC 19/08/1995 | View match | |
| Bristol Rovers FC v Gillingham FC 23/08/1995 | View match | |
| Gillingham FC v Cambridge United FC 26/08/1995 | View match | |
| Barnet FC v Gillingham FC 29/08/1995 | View match | |
| Gillingham FC v Colchester United FC 02/09/1995 | View match | |
| Scunthorpe United FC v Gillingham FC 09/09/1995 | View match | |
| Hereford United v Gillingham FC 12/09/1995 | View match | |
| Gillingham FC v Cardiff City FC 16/09/1995 | View match | |
| Chester City FC v Gillingham FC 23/09/1995 | View match | |
| Gillingham FC v Bury FC 30/09/1995 | £5.00 |