| West Ham United FC v Bolton Wanderers FC 21/03/1959 | £10.00 | |
| Manchester United FC v Bolton Wanderers FC 04/04/1959 | £10.00 | |
| Manchester United FC v Bolton Wanderers FC 04/04/1959 | £7.00 | |
| 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 | |
| Blackburn Rovers FC v Bolton Wanderers FC 24/09/1960 | £6.50 | |
| Bolton Wanderers FC v Manchester City FC 05/11/1960 | £7.50 | |
| Arsenal FC v Bolton Wanderers FC 10/12/1960 | £8.50 | |
| Blackburn Rovers FC v Bolton Wanderers FC 01/02/1961 | £7.50 | |
| Fulham FC v Bolton Wanderers FC 11/03/1961 | £5.50 |