| Gillingham FC v Torquay United FC 22/08/2000 | View match | |
| Gillingham FC v Portsmouth FC 25/08/2000 | View match | |
| Burnley FC v Gillingham FC 28/08/2000 | View match | |
| Gillingham FC v Wolverhampton Wanderers FC 02/09/2000 | View match | |
| Torquay United FC v Gillingham FC 05/09/2000 | View match | |
| Grimsby Town FC v Gillingham FC 09/09/2000 | View match | |
| Queens Park Rangers FC v Gillingham FC 13/09/2000 | £5.00 | |
| Gillingham FC v Huddersfield Town FC 16/09/2000 | View match | |
| Manchester City FC v Gillingham FC 20/09/2000 | £6.50 | |
| Fulham FC v Gillingham FC 23/09/2000 | View match | |
| Gillingham FC v Manchester City FC 26/09/2000 | View match | |
| Gillingham FC v Sheffield Wednesday FC 30/09/2000 | View match |