| Gillingham FC v Sheffield United FC 10/09/1988 | View match | |
| Huddersfield Town FC v Gillingham FC 17/09/1988 | View match | |
| Mansfield Town FC v Gillingham FC 20/09/1988 | View match | |
| Gillingham FC v Reading FC 24/09/1988 | View match | |
| Millwall FC v Gillingham FC 27/09/1988 | View match | |
| Brentford FC v Gillingham FC 01/10/1988 | View match | |
| Gillingham FC v Bristol City FC 04/10/1988 | View match | |
| Gillingham FC v Chesterfield FC 08/10/1988 | View match | |
| Gillingham FC v Millwall FC 11/10/1988 | View match | |
| Southend United FC v Gillingham FC 15/10/1988 | View match | |
| Gillingham FC v Bury FC 22/10/1988 | £5.00 | |
| Preston North End FC v Gillingham FC 25/10/1988 | View match |