| Gillingham FC v Orient 14/08/1968 | View match | |
| Gillingham FC v Orient 17/08/1968 | View match | |
| Orient v Gillingham FC 20/08/1968 | View match | |
| Barnsley FC v Gillingham FC 24/08/1968 | View match | |
| Rotherham United FC v Gillingham FC 27/08/1968 | View match | |
| Gillingham FC v Luton Town FC 31/08/1968 | View match | |
| Torquay United FC v Gillingham FC 07/09/1968 | View match | |
| Gillingham FC v Brighton & Hove Albion FC 14/09/1968 | View match | |
| Barrow v Gillingham FC 16/09/1968 | View match | |
| Southport v Gillingham FC 20/09/1968 | £6.50 | |
| Gillingham FC v Mansfield Town FC 28/09/1968 | View match | |
| Reading FC v Gillingham FC 04/10/1968 | £6.00 |