| Grimsby Town FC v Gillingham FC 17/10/1989 | View match | |
| Gillingham FC v Chesterfield FC 21/10/1989 | View match | |
| Gillingham FC v Rochdale FC 31/10/1989 | View match | |
| Gillingham FC v Scarborough FC 04/11/1989 | View match | |
| Southend United FC v Gillingham FC 07/11/1989 | View match | |
| Lincoln City FC v Gillingham FC 11/11/1989 | View match | |
| Torquay United FC v Gillingham FC 14/11/1989 | View match | |
| Gillingham FC v Welling United 18/11/1989 | View match | |
| Welling United v Gillingham FC 22/11/1989 | £4.50 | |
| Gillingham FC v Colchester United FC 24/11/1989 | View match | |
| Gillingham FC v Cambridge United FC 28/11/1989 | View match | |
| York City FC v Gillingham FC 09/12/1989 | View match |