| Arbroath FC v Dumbarton 26/02/1966 | View match | |
| Arbroath FC v East Fife FC 05/03/1966 | View match | |
| Stenhousemuir FC v Arbroath FC 12/03/1966 | View match | |
| Stranraer v Arbroath FC 19/03/1966 | View match | |
| Arbroath FC v Third Lanark 26/03/1966 | View match | |
| Airdrieonians (Old) v Arbroath FC 31/03/1966 | View match | |
| Albion Rovers FC v Arbroath FC 13/04/1966 | View match | |
| Arbroath FC v Brechin City FC 16/04/1966 | View match | |
| Third Lanark v Arbroath FC 20/04/1966 | View match | |
| Arbroath FC v Ayr United FC 23/04/1966 | View match | |
| Arbroath FC v Cowdenbeath FC 27/04/1966 | View match | |
| East Stirlingshire FC v Arbroath FC 30/04/1966 | View match |