| Blackburn Rovers FC v Wolverhampton Wanderers FC 13/09/1958 | £9.50 | |
| Bolton Wanderers FC v Wolverhampton Wanderers FC 06/10/1958 | £32.00 | |
| Arsenal FC v Wolverhampton Wanderers FC 18/10/1958 | £9.50 | |
| Leicester City FC v Wolverhampton Wanderers FC 13/12/1958 | £9.50 | |
| Manchester United FC v Wolverhampton Wanderers FC 21/02/1959 | £9.50 | |
| Preston North End FC v Wolverhampton Wanderers FC 28/03/1959 | £8.00 | |
| Manchester City FC v Wolverhampton Wanderers FC 05/09/1959 | £6.00 | |
| Manchester City FC v Wolverhampton Wanderers FC 05/09/1959 | £5.50 | |
| Fulham FC v Wolverhampton Wanderers FC 09/09/1959 | £5.50 | |
| Arsenal FC v Wolverhampton Wanderers FC 02/01/1960 | £7.50 | |
| Arsenal FC v Wolverhampton Wanderers FC 02/01/1960 | £5.50 | |
| Wolverhampton Wanderers FC v Manchester City FC 16/01/1960 | £11.50 |