| Bolton Wanderers FC v Manchester United FC 14/11/1959 | View match | |
| Preston North End FC v Bolton Wanderers FC 21/11/1959 | View match | |
| Bolton Wanderers FC v Leicester City FC 28/11/1959 | View match | |
| Burnley FC v Bolton Wanderers FC 05/12/1959 | View match | |
| Bolton Wanderers FC v Birmingham City FC 12/12/1959 | View match | |
| Bolton Wanderers FC v Blackpool FC 19/12/1959 | View match | |
| Bolton Wanderers FC v Wolverhampton Wanderers FC 26/12/1959 | View match | |
| Wolverhampton Wanderers FC v Bolton Wanderers FC 28/12/1959 | View match | |
| Everton FC v Bolton Wanderers FC 02/01/1960 | View match | |
| Bury FC v Bolton Wanderers FC 09/01/1960 | £7.50 | |
| Bolton Wanderers FC v Bury FC 13/01/1960 | £5.00 | |
| Bolton Wanderers FC v Bury FC 13/01/1960 | £4.50 |