| Barnsley FC v Cardiff City FC 20/12/1958 | View match | |
| Middlesbrough FC v Barnsley FC 26/12/1958 | View match | |
| Barnsley FC v Middlesbrough FC 27/12/1958 | View match | |
| Stoke City FC v Barnsley FC 27/12/1958 | View match | |
| Sunderland FC v Barnsley FC 01/01/1959 | View match | |
| Huddersfield Town FC v Barnsley FC 03/01/1959 | View match | |
| Brentford FC v Barnsley FC 10/01/1959 | View match | |
| Barnsley FC v Rotherham United FC 31/01/1959 | View match | |
| Scunthorpe United FC v Barnsley FC 31/01/1959 | View match | |
| Sheffield United FC v Barnsley FC 07/02/1959 | View match | |
| Barnsley FC v Brighton & Hove Albion FC 14/02/1959 | £7.99 | |
| Fulham FC v Barnsley FC 14/02/1959 | View match |