| Bradford Park Avenue v Gillingham FC 14/12/1963 | View match | |
| Gillingham FC v Southport 21/12/1963 | View match | |
| Chesterfield FC v Gillingham FC 26/12/1963 | View match | |
| Gillingham FC v Chesterfield FC 28/12/1963 | View match | |
| Gillingham FC v Rochdale FC 04/01/1964 | View match | |
| Exeter City FC v Gillingham FC 11/01/1964 | View match | |
| Gillingham FC v Hartlepool United 18/01/1964 | View match | |
| Darlington FC v Gillingham FC 01/02/1964 | View match | |
| Gillingham FC v Tranmere Rovers FC 08/02/1964 | View match | |
| Halifax Town A.F.C v Gillingham FC 15/02/1964 | View match | |
| Gillingham FC v Doncaster Rovers FC 22/02/1964 | View match | |
| Brighton & Hove Albion FC v Gillingham FC 29/02/1964 | £3.00 |