| Manchester United FC v Bolton Wanderers FC 18/01/1958 | £30.00 | |
| Bolton Wanderers FC v Manchester United FC 03/05/1958 | £11.50 | |
| Arsenal FC v Bolton Wanderers FC 09/09/1958 | £5.50 | |
| Bolton Wanderers FC v Wolverhampton Wanderers FC 06/10/1958 | £32.00 | |
| Bolton Wanderers FC v Preston North End FC 23/02/1959 | £4.00 | |
| West Ham United FC v Bolton Wanderers FC 21/03/1959 | £10.00 | |
| Manchester United FC v Bolton Wanderers FC 04/04/1959 | £7.00 | |
| Manchester United FC v Bolton Wanderers FC 04/04/1959 | £10.00 | |
| Bolton Wanderers FC v Bury FC 13/01/1960 | £5.50 | |
| Bolton Wanderers FC v Preston North End FC 09/04/1960 | £7.50 | |
| Manchester City FC v Bolton Wanderers FC 15/04/1960 | £5.00 | |
| Bolton Wanderers FC v Manchester City FC 18/04/1960 | £7.50 |