| 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 | |
| Southampton FC v Southend United FC 23/01/1960 | View match | |
| Southend United FC v York City FC 30/01/1960 | View match | |
| Southend United FC v Reading FC 06/02/1960 | View match | |
| Shrewsbury Town FC v Southend United FC 13/02/1960 | View match | |
| Southend United FC v Peterborough United FC 20/02/1960 | View match | |
| Southend United FC v Peterborough United FC 20/02/1960 | View match | |
| Southend United FC v Port Vale FC 22/02/1960 | View match | |
| Grimsby Town FC v Southend United FC 27/02/1960 | View match | |
| Southend United FC v Barnsley FC 29/02/1960 | View match |