| Swindon Town FC v Gillingham FC 25/05/1987 | View match | |
| Gillingham FC v Swindon Town FC 29/05/1987 | View match | |
| Gillingham FC v Blackpool FC 15/08/1987 | View match | |
| Gillingham FC v Brighton & Hove Albion FC 18/08/1987 | View match | |
| Grimsby Town FC v Gillingham FC 22/08/1987 | View match | |
| Brighton & Hove Albion FC v Gillingham FC 26/08/1987 | £3.50 | |
| Gillingham FC v Southend United FC 29/08/1987 | View match | |
| Wigan Athletic FC v Gillingham FC 31/08/1987 | View match | |
| Gillingham FC v Chesterfield FC 05/09/1987 | View match | |
| Fulham FC v Gillingham FC 12/09/1987 | £3.50 | |
| Gillingham FC v Sunderland FC 15/09/1987 | View match | |
| Gillingham FC v York City FC 19/09/1987 | View match |