| Bolton Wanderers FC v Preston North End FC 23/02/1959 | £4.00 | |
| Nottingham Forest FC v Bolton Wanderers FC 28/02/1959 | View match | |
| Bolton Wanderers FC v Chelsea FC 04/03/1959 | View match | |
| Blackpool FC v Bolton Wanderers FC 07/03/1959 | View match | |
| Bolton Wanderers FC v Aston Villa FC 18/03/1959 | View match | |
| West Ham United FC v Bolton Wanderers FC 21/03/1959 | £10.00 | |
| Bolton Wanderers FC v Leicester City FC 27/03/1959 | View match | |
| Bolton Wanderers FC v Tottenham Hotspur FC 28/03/1959 | View match | |
| Leicester City FC v Bolton Wanderers FC 30/03/1959 | View match | |
| Manchester United FC v Bolton Wanderers FC 04/04/1959 | £10.00 | |
| Manchester United FC v Bolton Wanderers FC 04/04/1959 | £7.00 | |
| Birmingham City FC v Bolton Wanderers FC 08/04/1959 | View match |