| Gillingham FC v Wigan Athletic FC 15/04/2000 | View match | |
| Burnley FC v Gillingham FC 18/04/2000 | View match | |
| Gillingham FC v Luton Town FC 22/04/2000 | View match | |
| Millwall FC v Gillingham FC 24/04/2000 | View match | |
| Gillingham FC v Brentford FC 29/04/2000 | View match | |
| Gillingham FC v Cardiff City FC 02/05/2000 | View match | |
| Wrexham FC v Gillingham FC 06/05/2000 | View match | |
| Stoke City FC v Gillingham FC 13/05/2000 | View match | |
| Gillingham FC v Stoke City FC 17/05/2000 | View match | |
| Wigan Athletic FC v Gillingham FC 28/05/2000 | View match | |
| Gillingham FC v Stockport County FC 12/08/2000 | View match | |
| Tranmere Rovers FC v Gillingham FC 19/08/2000 | View match |