| Gillingham FC v Bournemouth & Boscombe 17/09/1966 | View match | |
| Gillingham FC v Arsenal FC 21/09/1966 | £6.50 | |
| Gillingham FC v Arsenal FC 21/09/1966 | £7.50 | |
| Swansea Town v Gillingham FC 24/09/1966 | View match | |
| Gillingham FC v Middlesbrough FC 01/10/1966 | View match | |
| Gillingham FC v Peterborough United FC 05/10/1966 | View match | |
| Torquay United FC v Gillingham FC 08/10/1966 | View match | |
| Walsall FC v Gillingham FC 11/10/1966 | View match | |
| Gillingham FC v Brighton & Hove Albion FC 15/10/1966 | View match | |
| Bristol Rovers FC v Gillingham FC 18/10/1966 | View match | |
| Darlington FC v Gillingham FC 22/10/1966 | View match | |
| Gillingham FC v Queens Park Rangers FC 29/10/1966 | View match |