| Southend United FC v Queens Park Rangers FC 24/08/1959 | £4.50 | |
| Southend United FC v Bury FC 29/08/1959 | £6.50 | |
| Queens Park Rangers FC v Southend United FC 31/08/1959 | View match | |
| Barnsley FC v Southend United FC 05/09/1959 | View match | |
| Southend United FC v Mansfield Town FC 07/09/1959 | £15.99 | |
| Southend United FC v Southampton FC 12/09/1959 | View match | |
| Mansfield Town FC v Southend United FC 14/09/1959 | View match | |
| Reading FC v Southend United FC 19/09/1959 | View match | |
| Southend United FC v Bradford City FC 21/09/1959 | View match | |
| Southend United FC v Shrewsbury Town FC 26/09/1959 | View match | |
| Bradford City FC v Southend United FC 29/09/1959 | View match | |
| Port Vale FC v Southend United FC 03/10/1959 | View match |