| Gillingham FC v Chelmsford City 06/12/1986 | View match | |
| Bolton Wanderers FC v Gillingham FC 13/12/1986 | View match | |
| Gillingham FC v Northampton Town FC 16/12/1986 | View match | |
| Gillingham FC v Bristol Rovers FC 19/12/1986 | View match | |
| Fulham FC v Gillingham FC 26/12/1986 | £3.50 | |
| Gillingham FC v Swindon Town FC 27/12/1986 | View match | |
| Gillingham FC v Walsall FC 01/01/1987 | View match | |
| Notts County FC v Gillingham FC 03/01/1987 | View match | |
| Wigan Athletic FC v Gillingham FC 19/01/1987 | View match | |
| Gillingham FC v Colchester United FC 26/01/1987 | View match | |
| Middlesbrough FC v Gillingham FC 31/01/1987 | View match | |
| Gillingham FC v Rotherham United FC 03/02/1987 | View match |