| Montrose FC v Dumbarton 29/04/2000 | View match | |
| Dumbarton v East Fife FC 06/05/2000 | View match | |
| Hamilton Academicals v Dumbarton 05/08/2000 | View match | |
| Dumbarton v Ayr United FC 09/08/2000 | View match | |
| Dumbarton v Brechin City FC 12/08/2000 | View match | |
| Elgin City FC v Dumbarton 15/08/2000 | View match | |
| Peterhead v Dumbarton 19/08/2000 | View match | |
| Dumbarton v Livingston FC 22/08/2000 | View match | |
| Albion Rovers FC v Dumbarton 26/08/2000 | View match | |
| Arbroath FC v Dumbarton 02/09/2000 | View match | |
| Dumbarton v East Stirlingshire FC 09/09/2000 | View match | |
| Montrose FC v Dumbarton 16/09/2000 | View match |