| Dundee United FC v Morton FC 20/08/1969 | View match | |
| Heart Of Midlothian (Hearts) v Dundee United FC 23/08/1969 | View match | |
| Dundee United FC v St Mirren FC 27/08/1969 | View match | |
| Dundee United FC v Rangers (Glasgow) FC 30/08/1969 | View match | |
| Clyde v Dundee United FC 03/09/1969 | View match | |
| Morton FC v Dundee United FC 06/09/1969 | View match | |
| Dundee United FC v Airdrieonians (Old) 13/09/1969 | View match | |
| Dundee United FC v Newcastle United FC 15/09/1969 | £8.99 | |
| Dundee v Dundee United FC 20/09/1969 | View match | |
| Dundee United FC v St Johnstone FC 27/09/1969 | View match | |
| Newcastle United FC v Dundee United FC 01/10/1969 | £8.99 | |
| Motherwell FC v Dundee United FC 04/10/1969 | View match |