| Exeter City FC v Gillingham FC 13/10/1956 | View match | |
| Gillingham FC v Southampton FC 20/10/1956 | View match | |
| Coventry City FC v Gillingham FC 27/10/1956 | View match | |
| Gillingham FC v Norwich City FC 03/11/1956 | View match | |
| Colchester United FC v Gillingham FC 10/11/1956 | View match | |
| Yiewsley v Gillingham FC 17/11/1956 | View match | |
| Gillingham FC v Yiewsley 21/11/1956 | View match | |
| Reading FC v Gillingham FC 24/11/1956 | View match | |
| Gillingham FC v Plymouth Argyle FC 01/12/1956 | View match | |
| Gillingham FC v Newport County 08/12/1956 | View match | |
| Watford FC v Gillingham FC 15/12/1956 | View match | |
| Gillingham FC v Shrewsbury Town FC 22/12/1956 | View match |