| Clyde v Hibernian FC 17/08/1999 | View match | |
| Clyde v Stranraer 21/08/1999 | View match | |
| Clyde v Stirling Albion FC 28/08/1999 | View match | |
| Clyde v Partick Thistle FC 11/09/1999 | View match | |
| Ross County FC v Clyde 18/09/1999 | View match | |
| Clyde v Hamilton Academicals 25/09/1999 | View match | |
| Stenhousemuir FC v Clyde 02/10/1999 | View match | |
| Clyde v Arbroath FC 16/10/1999 | View match | |
| Alloa Athletic FC v Clyde 23/10/1999 | View match | |
| Partick Thistle FC v Clyde 30/10/1999 | View match | |
| Clyde v Ross County FC 06/11/1999 | View match | |
| Clyde v Queen Of The South FC 09/11/1999 | View match |