| Bolton Wanderers FC v Preston North End FC 21/04/1958 | View match | |
| Burnley FC v Bolton Wanderers FC 26/04/1958 | View match | |
| Bolton Wanderers FC v Manchester United FC 03/05/1958 | £9.50 | |
| Bolton Wanderers FC v Manchester United FC 03/05/1958 | £9.50 | |
| Bolton Wanderers FC v Leeds United FC 23/08/1958 | View match | |
| Manchester City FC v Bolton Wanderers FC 27/08/1958 | View match | |
| West Bromwich Albion FC v Bolton Wanderers FC 30/08/1958 | View match | |
| Bolton Wanderers FC v Manchester City FC 03/09/1958 | View match | |
| Bolton Wanderers FC v Birmingham City FC 06/09/1958 | £12.99 | |
| Arsenal FC v Bolton Wanderers FC 09/09/1958 | £5.50 | |
| Luton Town FC v Bolton Wanderers FC 13/09/1958 | View match | |
| Bolton Wanderers FC v Arsenal FC 17/09/1958 | View match |