| Reading FC v Gillingham FC 04/10/1968 | £6.00 | |
| Gillingham FC v Stockport County FC 12/10/1968 | £5.50 | |
| Orient v Gillingham FC 16/11/1968 | £6.99 | |
| Gillingham FC v Bristol Rovers FC 21/12/1968 | £5.50 | |
| Orient v Gillingham FC 08/03/1969 | £9.99 | |
| Gillingham FC v Southport 12/04/1969 | £6.99 | |
| Brighton & Hove Albion FC v Gillingham FC 19/04/1969 | £4.50 | |
| Aldershot F.C v Gillingham FC 13/08/1969 | £8.50 | |
| Fulham FC v Gillingham FC 23/08/1969 | £4.00 | |
| Fulham FC v Gillingham FC 23/08/1969 | £4.00 | |
| Brighton & Hove Albion FC v Gillingham FC 06/09/1969 | £3.00 | |
| Gillingham FC v Southport 01/10/1969 | £6.00 |