| Hartlepool United v Gillingham FC 10/03/1969 | View match | |
| Gillingham FC v Barnsley FC 14/03/1969 | View match | |
| Luton Town FC v Gillingham FC 22/03/1969 | View match | |
| Gillingham FC v Crewe Alexandra FC 26/03/1969 | View match | |
| Gillingham FC v Torquay United FC 29/03/1969 | View match | |
| Oldham Athletic FC v Gillingham FC 04/04/1969 | View match | |
| Mansfield Town FC v Gillingham FC 05/04/1969 | View match | |
| Gillingham FC v Barrow 07/04/1969 | View match | |
| 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 |