| Gillingham FC v Brentford FC 03/11/1987 | View match | |
| Gillingham FC v Brighton & Hove Albion FC 07/11/1987 | £4.50 | |
| Gillingham FC v Fulham FC 14/11/1987 | View match | |
| Northampton Town FC v Gillingham FC 21/11/1987 | View match | |
| Gillingham FC v Walsall FC 05/12/1987 | View match | |
| Rotherham United FC v Gillingham FC 12/12/1987 | View match | |
| Gillingham FC v Walsall FC 18/12/1987 | View match | |
| Gillingham FC v Bristol City FC 26/12/1987 | View match | |
| Aldershot F.C v Gillingham FC 28/12/1987 | View match | |
| Southend United FC v Gillingham FC 01/01/1988 | View match | |
| Gillingham FC v Fulham FC 02/01/1988 | View match | |
| Gillingham FC v Birmingham City FC 09/01/1988 | View match |