| Grimsby Town FC v Derby County FC 08/11/1958 | View match | |
| Bristol Rovers FC v Grimsby Town FC 15/11/1958 | View match | |
| Grimsby Town FC v Ipswich Town FC 22/11/1958 | View match | |
| Swansea Town v Grimsby Town FC 29/11/1958 | View match | |
| Grimsby Town FC v Stoke City FC 06/12/1958 | View match | |
| Leyton Orient FC v Grimsby Town FC 13/12/1958 | £6.00 | |
| Grimsby Town FC v Liverpool FC 20/12/1958 | View match | |
| Grimsby Town FC v Sheffield United FC 25/12/1958 | View match | |
| Sheffield United FC v Grimsby Town FC 27/12/1958 | View match | |
| Grimsby Town FC v Manchester City FC 10/01/1959 | View match | |
| Manchester City FC v Grimsby Town FC 24/01/1959 | £7.00 | |
| Nottingham Forest FC v Grimsby Town FC 28/01/1959 | View match |