| Port Vale FC v Shrewsbury Town FC 22/11/1958 | £15.00 | |
| Darlington FC v Port Vale FC 29/11/1958 | View match | |
| Millwall FC v Port Vale FC 13/12/1958 | View match | |
| Northampton Town FC v Port Vale FC 20/12/1958 | View match | |
| Port Vale FC v Gateshead 26/12/1958 | £15.00 | |
| Gateshead v Port Vale FC 01/01/1959 | View match | |
| Port Vale FC v Walsall FC 23/01/1959 | View match | |
| Port Vale FC v Bradford Park Avenue 31/01/1959 | View match | |
| Port Vale FC v Aldershot F.C 07/02/1959 | View match | |
| Crystal Palace FC v Port Vale FC 14/02/1959 | View match | |
| Port Vale FC v Chester City FC 21/02/1959 | View match | |
| Oldham Athletic FC v Port Vale FC 28/02/1959 | View match |