| Southend United FC v Newport County 30/03/1959 | View match | |
| Southend United FC v Hull City FC 04/04/1959 | View match | |
| Southend United FC v Brentford FC 08/04/1959 | View match | |
| Mansfield Town FC v Southend United FC 11/04/1959 | View match | |
| Newport County v Southend United FC 13/04/1959 | View match | |
| Southend United FC v Swindon Town FC 18/04/1959 | £8.00 | |
| Brentford FC v Southend United FC 25/04/1959 | View match | |
| Southend United FC v Portsmouth FC 27/04/1959 | View match | |
| Southend United FC v Notts County FC 29/04/1959 | View match | |
| Halifax Town A.F.C v Southend United FC 22/08/1959 | View match | |
| Southend United FC v Queens Park Rangers FC 24/08/1959 | £4.50 | |
| Southend United FC v Bury FC 29/08/1959 | £6.50 |