| Brighton & Hove Albion FC v Gillingham FC 26/12/1956 | £8.00 | |
| Walsall FC v Gillingham FC 29/12/1956 | £30.00 | |
| Northampton Town FC v Gillingham FC 05/01/1957 | View match | |
| Gillingham FC v Ipswich Town FC 12/01/1957 | View match | |
| Bournemouth & Boscombe v Gillingham FC 19/01/1957 | View match | |
| Gillingham FC v Northampton Town FC 26/01/1957 | View match | |
| Gillingham FC v Torquay United FC 02/02/1957 | View match | |
| Millwall FC v Gillingham FC 09/02/1957 | View match | |
| Crystal Palace FC v Gillingham FC 16/02/1957 | View match | |
| Gillingham FC v Exeter City FC 23/02/1957 | View match | |
| Southampton FC v Gillingham FC 02/03/1957 | View match | |
| Gillingham FC v Queens Park Rangers FC 09/03/1957 | View match |