| Montrose FC v East Fife FC 04/02/1989 | View match | |
| Montrose FC v Stranraer 22/02/1989 | View match | |
| Stenhousemuir FC v Montrose FC 01/03/1989 | View match | |
| Queens Park FC v Montrose FC 04/03/1989 | View match | |
| Albion Rovers FC v Montrose FC 07/03/1989 | View match | |
| Montrose FC v Cowdenbeath FC 11/03/1989 | View match | |
| Montrose FC v Brechin City FC 25/03/1989 | View match | |
| Dumbarton v Montrose FC 28/03/1989 | View match | |
| Stenhousemuir FC v Montrose FC 01/04/1989 | View match | |
| Montrose FC v East Stirlingshire FC 08/04/1989 | View match | |
| Montrose FC v Arbroath FC 15/04/1989 | View match | |
| Alloa Athletic FC v Montrose FC 22/04/1989 | View match |