| 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 | |
| Gillingham FC v Bristol Rovers FC 17/09/1969 | View match | |
| Rotherham United FC v Gillingham FC 20/09/1969 | View match | |
| Gillingham FC v Barnsley FC 27/09/1969 | View match | |
| Gillingham FC v Southport 01/10/1969 | £6.00 | |
| Torquay United FC v Gillingham FC 04/10/1969 | View match | |
| Reading FC v Gillingham FC 08/10/1969 | £2.00 | |
| Gillingham FC v Tranmere Rovers FC 11/10/1969 | View match | |
| Barrow v Gillingham FC 18/10/1969 | View match |