| Preston North End FC v Gillingham FC 26/09/1998 | View match | |
| Gillingham FC v Macclesfield Town FC 03/10/1998 | View match | |
| Gillingham FC v Wycombe Wanderers FC 10/10/1998 | View match | |
| Reading FC v Gillingham FC 17/10/1998 | View match | |
| AFC Bournemouth v Gillingham FC 20/10/1998 | View match | |
| Gillingham FC v Luton Town FC 24/10/1998 | View match | |
| Lincoln City FC v Gillingham FC 31/10/1998 | View match | |
| Gillingham FC v Wigan Athletic FC 07/11/1998 | View match | |
| Gillingham FC v Oldham Athletic FC 10/11/1998 | View match | |
| Oldham Athletic FC v Gillingham FC 14/11/1998 | View match | |
| Manchester City FC v Gillingham FC 21/11/1998 | £5.00 | |
| Gillingham FC v Fulham FC 28/11/1998 | View match |