| Gillingham FC v Southport 12/04/1969 | £6.99 | |
| Gillingham FC v Oldham Athletic FC 16/04/1969 | View match | |
| Brighton & Hove Albion FC v Gillingham FC 19/04/1969 | £4.50 | |
| Gillingham FC v Bournemouth & Boscombe 22/04/1969 | View match | |
| 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 |