| Southport v York City FC 02/09/1958 | View match | |
| Coventry City FC v Southport 06/09/1958 | View match | |
| Southport v Bradford Park Avenue 09/09/1958 | View match | |
| Torquay United FC v Southport 13/09/1958 | View match | |
| Bradford Park Avenue v Southport 15/09/1958 | View match | |
| Southport v Crewe Alexandra FC 20/09/1958 | View match | |
| Southport v Port Vale FC 23/09/1958 | View match | |
| Northampton Town FC v Southport 27/09/1958 | View match | |
| Port Vale FC v Southport 29/09/1958 | View match | |
| Southport v Workington 04/10/1958 | View match | |
| Crystal Palace FC v Southport 08/10/1958 | View match | |
| Southport v Darlington FC 11/10/1958 | View match |