| Walsall FC v Gillingham FC 11/12/1999 | View match | |
| Gillingham FC v Colchester United FC 26/12/1999 | View match | |
| Wigan Athletic FC v Gillingham FC 28/12/1999 | View match | |
| Gillingham FC v Reading FC 03/01/2000 | View match | |
| Gillingham FC v Walsall FC 08/01/2000 | View match | |
| Gillingham FC v Bradford City FC 11/01/2000 | View match | |
| Bristol Rovers FC v Gillingham FC 15/01/2000 | View match | |
| Gillingham FC v Blackpool FC 22/01/2000 | View match | |
| Gillingham FC v Sheffield Wednesday FC 29/01/2000 | ||
| Chesterfield FC v Gillingham FC 01/02/2000 | View match | |
| Gillingham FC v Stoke City FC 05/02/2000 | View match | |
| Oldham Athletic FC v Gillingham FC 12/02/2000 | View match |