| Chesterfield FC v Gillingham FC 25/01/1986 | View match | |
| Gillingham FC v Brentford FC 29/01/1986 | View match | |
| Gillingham FC v Notts County FC 01/02/1986 | View match | |
| Gillingham FC v AFC Bournemouth 08/02/1986 | View match | |
| Wigan Athletic FC v Gillingham FC 15/02/1986 | View match | |
| Gillingham FC v Bury FC 22/02/1986 | £3.00 | |
| Gillingham FC v Bury FC 22/02/1986 | £3.00 | |
| York City FC v Gillingham FC 01/03/1986 | View match | |
| Gillingham FC v Plymouth Argyle FC 04/03/1986 | View match | |
| Gillingham FC v Blackpool FC 08/03/1986 | View match | |
| Cardiff City FC v Gillingham FC 15/03/1986 | View match | |
| Gillingham FC v Brentford FC 18/03/1986 | View match |