| Arbroath FC v Stranraer 22/11/2008 | View match | |
| East Fife FC v Arbroath FC 29/11/2008 | View match | |
| Queens Park FC v Arbroath FC 06/12/2008 | View match | |
| Arbroath FC v Peterhead 13/12/2008 | View match | |
| Raith Rovers FC v Arbroath FC 20/12/2008 | View match | |
| Arbroath FC v Stirling Albion FC 27/12/2008 | View match | |
| Arbroath FC v East Fife FC 17/01/2009 | View match | |
| Ayr United FC v Arbroath FC 25/01/2009 | View match | |
| Arbroath FC v Alloa Athletic FC 31/01/2009 | View match | |
| Stranraer v Arbroath FC 14/02/2009 | View match | |
| Arbroath FC v Queens Park FC 21/02/2009 | View match | |
| Stirling Albion FC v Arbroath FC 28/02/2009 | View match |