| Montrose FC v Dumbarton 14/03/2009 | View match | |
| Albion Rovers FC v Dumbarton 17/03/2009 | View match | |
| Dumbarton v Annan Athletic FC 21/03/2009 | View match | |
| Elgin City FC v Dumbarton 31/03/2009 | View match | |
| Stenhousemuir FC v Dumbarton 04/04/2009 | View match | |
| Forfar Athletic FC v Dumbarton 07/04/2009 | View match | |
| Dumbarton v Berwick Rangers FC 11/04/2009 | View match | |
| Cowdenbeath FC v Dumbarton 18/04/2009 | View match | |
| Dumbarton v Forfar Athletic FC 25/04/2009 | View match | |
| Dumbarton v Elgin City FC 02/05/2009 | View match | |
| Annan Athletic FC v Dumbarton 09/05/2009 | View match | |
| Dumbarton v Dunfermline Athletic 01/08/2009 | View match |