| Gillingham FC v Chesterfield FC 06/02/1999 | View match | |
| Northampton Town FC v Gillingham FC 13/02/1999 | View match | |
| Gillingham FC v Colchester United FC 20/02/1999 | View match | |
| Bristol Rovers FC v Gillingham FC 23/02/1999 | View match | |
| Burnley FC v Gillingham FC 27/02/1999 | View match | |
| Gillingham FC v Preston North End FC 06/03/1999 | View match | |
| Macclesfield Town FC v Gillingham FC 09/03/1999 | View match | |
| Wigan Athletic FC v Gillingham FC 13/03/1999 | View match | |
| Gillingham FC v Lincoln City FC 20/03/1999 | View match | |
| 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 |