| Alloa Athletic FC v Stranraer 27/11/1999 | View match | |
| Stranraer v Arbroath FC 04/12/1999 | View match | |
| Stirling Albion FC v Stranraer 18/12/1999 | View match | |
| Stranraer v Clyde 27/12/1999 | View match | |
| Stranraer v Queen Of The South FC 03/01/2000 | View match | |
| Stranraer v Clachnacuddin 08/01/2000 | View match | |
| Hamilton Academicals v Stranraer 15/01/2000 | View match | |
| Arbroath FC v Stranraer 22/01/2000 | View match | |
| Stranraer v Berwick Rangers FC 29/01/2000 | View match | |
| Stenhousemuir FC v Stranraer 12/02/2000 | View match | |
| Stranraer v Ross County FC 26/02/2000 | View match | |
| Stranraer v Partick Thistle FC 07/03/2000 | View match |