| Queens Park FC v Stranraer 31/01/2009 | View match | |
| Stranraer v Brechin City FC 07/02/2009 | View match | |
| Stranraer v Arbroath FC 14/02/2009 | View match | |
| Peterhead v Stranraer 21/02/2009 | View match | |
| Stranraer v Alloa Athletic FC 28/02/2009 | View match | |
| Stranraer v Peterhead 04/03/2009 | View match | |
| Ayr United FC v Stranraer 07/03/2009 | View match | |
| Brechin City FC v Stranraer 10/03/2009 | View match | |
| Stranraer v Queens Park FC 14/03/2009 | View match | |
| East Fife FC v Stranraer 21/03/2009 | View match | |
| Stranraer v Ayr United FC 28/03/2009 | View match | |
| Stranraer v Raith Rovers FC 04/04/2009 | View match |