| Southend United FC v Tranmere Rovers FC 24/10/1959 | View match | |
| Coventry City FC v Southend United FC 31/10/1959 | View match | |
| Southend United FC v Accrington Stanley (1891) 07/11/1959 | View match | |
| Southend United FC v Oswestry Town F.C 14/11/1959 | View match | |
| Southend United FC v Chesterfield FC 21/11/1959 | View match | |
| Swindon Town FC v Southend United FC 28/11/1959 | View match | |
| Southampton FC v Southend United FC 05/12/1959 | £6.50 | |
| Bournemouth & Boscombe v Southend United FC 12/12/1959 | View match | |
| Southend United FC v Halifax Town A.F.C 19/12/1959 | View match | |
| Southend United FC v Brentford FC 26/12/1959 | View match | |
| Brentford FC v Southend United FC 28/12/1959 | £6.50 | |
| Bury FC v Southend United FC 02/01/1960 | £7.50 |