| 1 | 31/8/2019 | 2-1 v MontroseMontrose 1-2 Dumbarton | Ladbrokes League One |
| 2 | 14/9/2019 | 0-1 v AirdrieoniansDumbarton 0-1 Airdrieonians | Ladbrokes League One |
| 3 | 21/9/2019 | 2-2 v East FifeEast Fife 2-2 Dumbarton | Ladbrokes League One |
| 4 | 28/9/2019 | 1-2 v ClydeDumbarton 1-2 Clyde | Ladbrokes League One |
| 5 | 19/10/2019 | 0-0 v StranraerStranraer 0-0 Dumbarton | Ladbrokes League One |
| 6 | 26/10/2019 | 1-0 v PeterheadDumbarton 1-0 Peterhead | Ladbrokes League One |
| 7 | 2/11/2019 | 1-3 v AirdrieoniansAirdrieonians 3-1 Dumbarton | Ladbrokes League One |
| 8 | 9/11/2019 | 2-4 v East FifeDumbarton 2-4 East Fife | Ladbrokes League One |
| 9 | 16/11/2019 | 1-1 v FalkirkDumbarton 1-1 Falkirk | Ladbrokes League One |
| 10 | 30/11/2019 | 2-1 v ClydeClyde 1-2 Dumbarton | Ladbrokes League One |
| 11 | 7/12/2019 | 0-2 v MontroseDumbarton 0-2 Montrose | Ladbrokes League One |
| 12 | 14/12/2019 | 4-3 v Forfar AthleticForfar Athletic 3-4 Dumbarton | Ladbrokes League One |
| 13 | 28/12/2019 | 1-1 v StranraerDumbarton 1-1 Stranraer | Ladbrokes League One |
| 14 | 4/1/2020 | 0-3 v FalkirkFalkirk 3-0 Dumbarton | Ladbrokes League One |
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