| Manchester United FC v Tottenham Hotspur FC 12/09/1959 | View match | |
| Leeds United FC v Manchester United FC 16/09/1959 | View match | |
| Manchester City FC v Manchester United FC 19/09/1959 | £8.50 | |
| Preston North End FC v Manchester United FC 26/09/1959 | View match | |
| Manchester United FC v Real Madrid 01/10/1959 | £5.00 | |
| Manchester United FC v Leicester City FC 03/10/1959 | View match | |
| Manchester United FC v Arsenal FC 10/10/1959 | £4.50 | |
| Wolverhampton Wanderers FC v Manchester United FC 17/10/1959 | View match | |
| Manchester United FC v Sheffield Wednesday FC 24/10/1959 | £5.00 | |
| Home Farm (Dublin) v Manchester United FC 26/10/1959 | View match | |
| Blackburn Rovers FC v Manchester United FC 31/10/1959 | £9.00 | |
| Manchester United FC v Fulham FC 07/11/1959 | View match |