| Luton Town FC v Gillingham FC 27/03/1999 | £4.00 | |
| Gillingham FC v Reading FC 01/04/1999 | View match | |
| Wycombe Wanderers FC v Gillingham FC 05/04/1999 | View match | |
| Gillingham FC v AFC Bournemouth 09/04/1999 | View match | |
| Fulham FC v Gillingham FC 13/04/1999 | £3.50 | |
| Gillingham FC v Manchester City FC 17/04/1999 | View match | |
| Wrexham FC v Gillingham FC 20/04/1999 | View match | |
| Oldham Athletic FC v Gillingham FC 24/04/1999 | View match | |
| Gillingham FC v Stoke City FC 01/05/1999 | View match | |
| Notts County FC v Gillingham FC 08/05/1999 | View match | |
| Preston North End FC v Gillingham FC 16/05/1999 | View match | |
| Gillingham FC v Preston North End FC 19/05/1999 | View match |