| Luton Town FC v Gillingham FC 16/10/1999 | View match | |
| Brentford FC v Gillingham FC 19/10/1999 | View match | |
| Gillingham FC v Cambridge United FC 23/10/1999 | View match | |
| Cheltenham Town FC v Gillingham FC 30/10/1999 | View match | |
| Gillingham FC v Bristol City FC 02/11/1999 | View match | |
| Notts County FC v Gillingham FC 06/11/1999 | View match | |
| Gillingham FC v Cheltenham Town FC 09/11/1999 | View match | |
| Gillingham FC v AFC Bournemouth 12/11/1999 | View match | |
| Gillingham FC v Darlington FC 20/11/1999 | View match | |
| Scunthorpe United FC v Gillingham FC 23/11/1999 | View match | |
| Cardiff City FC v Gillingham FC 27/11/1999 | View match | |
| Gillingham FC v Bury FC 04/12/1999 | £6.00 |