| Stirling Albion FC v Clyde 20/11/1999 | View match | |
| Clyde v Stenhousemuir FC 27/11/1999 | View match | |
| Hamilton Academicals v Clyde 04/12/1999 | View match | |
| Hamilton Academicals v Clyde 11/12/1999 | View match | |
| Clyde v Alloa Athletic FC 18/12/1999 | View match | |
| Stranraer v Clyde 27/12/1999 | View match | |
| Cowdenbeath FC v Clyde 08/01/2000 | View match | |
| Clyde v Hamilton Academicals 22/01/2000 | View match | |
| Clyde v Raith Rovers FC 29/01/2000 | View match | |
| Clyde v Raith Rovers FC 29/01/2000 | View match | |
| Stenhousemuir FC v Clyde 05/02/2000 | View match | |
| Clyde v Stirling Albion FC 12/02/2000 | View match |