| 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 | |
| Colchester United FC v Gillingham FC 05/12/1998 | View match | |
| Stoke City FC v Gillingham FC 12/12/1998 | View match | |
| Gillingham FC v Notts County FC 19/12/1998 | View match | |
| Gillingham FC v Millwall FC 29/12/1998 | View match | |
| Gillingham FC v Blackpool FC 02/01/1999 | View match | |
| Walsall FC v Gillingham FC 09/01/1999 | View match | |
| Gillingham FC v York City FC 16/01/1999 | View match | |
| Millwall FC v Gillingham FC 30/01/1999 | View match |