| Gillingham FC v Aldershot F.C 29/08/1956 | View match | |
| Gillingham FC v Walsall FC 01/09/1956 | View match | |
| Gillingham FC v Swindon Town FC 05/09/1956 | View match | |
| Ipswich Town FC v Gillingham FC 08/09/1956 | View match | |
| Swindon Town FC v Gillingham FC 12/09/1956 | View match | |
| Gillingham FC v Bournemouth & Boscombe 15/09/1956 | View match | |
| Brentford FC v Gillingham FC 18/09/1956 | £16.50 | |
| Torquay United FC v Gillingham FC 22/09/1956 | View match | |
| Gillingham FC v Brentford FC 26/09/1956 | View match | |
| Gillingham FC v Millwall FC 29/09/1956 | View match | |
| Gillingham FC v Crystal Palace FC 06/10/1956 | View match | |
| Exeter City FC v Gillingham FC 13/10/1956 | View match |