| Crewe Alexandra FC v Gillingham FC 30/04/1969 | View match | |
| Shrewsbury Town FC v Gillingham FC 05/05/1969 | View match | |
| Mansfield Town FC v Gillingham FC 09/08/1969 | View match | |
| Aldershot F.C v Gillingham FC 13/08/1969 | £8.50 | |
| Gillingham FC v Reading FC 16/08/1969 | View match | |
| Fulham FC v Gillingham FC 23/08/1969 | £4.00 | |
| Fulham FC v Gillingham FC 23/08/1969 | £4.00 | |
| Stockport County FC v Gillingham FC 25/08/1969 | View match | |
| Gillingham FC v Luton Town FC 30/08/1969 | View match | |
| Blackpool FC v Gillingham FC 03/09/1969 | View match | |
| Brighton & Hove Albion FC v Gillingham FC 06/09/1969 | £3.00 | |
| Gillingham FC v Rochdale FC 13/09/1969 | View match |