| Port Vale FC v Southend United FC 15/02/1958 | View match | |
| Southend United FC v Bournemouth & Boscombe 22/02/1958 | View match | |
| Walsall FC v Southend United FC 01/03/1958 | £35.00 | |
| Southend United FC v Coventry City FC 08/03/1958 | View match | |
| Shrewsbury Town FC v Southend United FC 15/03/1958 | View match | |
| Southend United FC v Watford FC 22/03/1958 | View match | |
| Brentford FC v Southend United FC 29/03/1958 | £8.50 | |
| Gillingham FC v Southend United FC 04/04/1958 | View match | |
| Southend United FC v Reading FC 05/04/1958 | View match | |
| Southend United FC v Gillingham FC 07/04/1958 | View match | |
| Crystal Palace FC v Southend United FC 12/04/1958 | View match | |
| Southend United FC v Plymouth Argyle FC 16/04/1958 | View match |