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| July 2019 | |||||
| Date | Kick Off | Opposition | Competition | Score | Report |
| 6th | 15:00 | Airdrieonians (A) | Friendly | 0-3 |  |
| 9th | 19:45 | Raith Rovers (A) | Friendly | 1-2 | |
| 13th | 15:00 | East Fife FC (H) | Betfred Cup | 2-0 | |
| 16th | 19:45 | Heart of Midlothian (H) | Betfred Cup | 0-2 | |
| 19th | 19:45 | Dundee United FC (A) | Betfred Cup | 0-3 | |
| 27th | 15:00 | Stenhousemuir (A) | Betfred Cup | 0-2 | |
| August 2019 | |||||
| Date | Kick Off | Opposition | Competition | Score | Report |
| 3rd | 15:00 | Elgin City (A) | Ladbrokes League 2 | 0-3 | |
| 10th | 15:00 | Stirling Albion (H) | Ladbrokes League 2 | 1-0 | |
| 13th | 19:45 | Heart of Midlothian U21 (A) | Challenge Cup | 1-3 | |
| 17th | 15:00 | Cove Rangers (A) | Ladbrokes League 2 | 2-3 | |
| 24th | 15:00 | Annan Athletic (H) | Ladbrokes League 2 | 3-1 | |
| 31st | 15:00 | Brechin City (H) | Ladbrokes League 2 | 2-1 | |
| September 2019 | |||||
| Date | Kick Off | Opposition | Competition | Score | Report |
| 14th | 15:00 | Stenhousemuir (A) | Ladbrokes League 2 | 3-0 | |
| 21st | 15:00 | Queen's Park (A) | Ladbrokes League 2 | 3-0 | |
| 28th | 15:00 | Albion Rovers (H) | Ladbrokes League 2 | 1-0 | |
| October 2019 | |||||
| Date | Kick Off | Opposition | Competition | Score | Report |
| 5th | 15:00 | Edinburgh City (H) | Ladbrokes League 2 | 1-0 | |
| 8th | 19:45 | Kelty Hearts (H) | Fife Cup | 4-0 | |
| 19th | 15:00 | Broxburn Athletic (H) | Scottish Cup | 1-1 | |
| 26th | 15:00 | Broxburn Athletic (A) | Scottish Cup | 0-3 | |
| 29th | 19:45 | Stirling Albion (A) | Ladbrokes League 2 | 0-0 | |
| November 2019 | |||||
| Date | Kick Off | Opposition | Competition | Score | Report |
| 2nd | 15:00 | Cove Rangers (H) | Ladbrokes League 2 | 1-3 | |
| 9th | 15:00 | Annan Athletic (A) | Ladbrokes League 2 | 0-1 | |
| 16th | 15:00 | Queen's Park (H) | Ladbrokes League 2 | 1-0 | |
| December 2019 | |||||
| Date | Kick Off | Opposition | Competition | Score | Report |
| 7th | 15:00 | Elgin City (H) | Ladbrokes League 2 | 0-0 | |
| 14th | 15:00 | Brechin City (A) | Ladbrokes League 2 | 1-2 | |
| 21st | 15:00 | Stenhousemuir (H) | Ladbrokes League 2 | 3-1 | |
| 28th | 15:00 | Edinburgh City (A) | Ladbrokes League 2 | 0-2 | |
| January 2020 | |||||
| Date | Kick Off | Opposition | Competition | Score | Report |
| 4th | 15:00 | Annan Athletic (H) | Ladbrokes League 2 | 3-1 | |
| 18th | 15:00 | Cove Rangers (A) | Ladbrokes League 2 | 1-3 | |
| 25th | 15:00 | Brechin City (H) | Ladbrokes League 2 | 3-2 | |
| February 2020 | |||||
| Date | Kick Off | Opposition | Competition | Score | Report |
| 1st | 15:00 | Queen's Park (A) | Ladbrokes League 2 | 0-1 | |
| 8th | 15:00 | Stenhousemuir (A) | Ladbrokes League 2 | 2-2 | |
| 15th | 15:00 | Stirling Albion (H) | Ladbrokes League 2 | 1-4 | |
| 29th | 15:00 | Edinburgh City (H) | Ladbrokes League 2 | 1-1 | |
| March 2020 | |||||
| Date | Kick Off | Opposition | Competition | Score | Report |
| 3rd | 19:45 | Albion Rovers (H) | Ladbrokes League 2 | 2-1 | |
| 7th | 15:00 | Annan Athletic (A) | Ladbrokes League 2 | 0-0 | |
| 10th | 19:45 | Elgin City (A) | Ladbrokes League 2 | 2-3 | |
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