| 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 | |
| Stoke City FC v Gillingham FC 22/09/1987 | View match | |
| Bristol City FC v Gillingham FC 26/09/1987 | View match | |
| Gillingham FC v Chester City FC 29/09/1987 | View match | |
| Doncaster Rovers FC v Gillingham FC 03/10/1987 | View match | |
| Gillingham FC v Stoke City FC 06/10/1987 | View match | |
| Gillingham FC v Bristol Rovers FC 10/10/1987 | View match | |
| Aldershot F.C v Gillingham FC 13/10/1987 | View match | |
| Mansfield Town FC v Gillingham FC 17/10/1987 | View match | |
| Preston North End FC v Gillingham FC 20/10/1987 | View match |