| Gillingham FC v Southend United FC 25/02/1989 | View match | |
| Gillingham FC v Preston North End FC 28/02/1989 | View match | |
| Bury FC v Gillingham FC 04/03/1989 | View match | |
| Gillingham FC v Cardiff City FC 11/03/1989 | View match | |
| Wolverhampton Wanderers FC v Gillingham FC 14/03/1989 | View match | |
| Swansea City FC v Gillingham FC 19/03/1989 | View match | |
| Gillingham FC v Wigan Athletic FC 24/03/1989 | View match | |
| Fulham FC v Gillingham FC 27/03/1989 | £4.00 | |
| Gillingham FC v Northampton Town FC 01/04/1989 | View match | |
| Gillingham FC v Bolton Wanderers FC 04/04/1989 | View match | |
| Port Vale FC v Gillingham FC 08/04/1989 | View match | |
| Gillingham FC v Mansfield Town FC 15/04/1989 | View match |