| Cape Breton | 1 | @ | Highland FC | 3 | F | Nov 04, 2018 | Details | 3 pts |
| Highland FC | 3 | @ | Valley United | 0 | F | Nov 10, 2018 | Details | 3 pts |
| Halifax Dunbrack | 0 | @ | Highland FC | 7 | F | Nov 18, 2018 | Details | 3 pts |
| Highland FC | 4 | @ | Suburban FC | 1 | F | Nov 24, 2018 | Details | 3 pts |
| Highland FC | 2 | @ | Halifax City White | 1 | F | Nov 25, 2018 | Details | 3 pts |
| Halifax City Green | 1 | @ | Highland FC | 4 | F | Dec 02, 2018 | Details | 3 pts |
| Highland FC | 6 | @ | United DFC | 3 | F | Dec 09, 2018 | Details | 3 pts |
| Highland FC | 5 | @ | Cape Breton | 2 | F | Jan 13, 2019 | Details | 3 pts |
| Suburban FC | 3 | @ | Highland FC | 3 | F | Jan 27, 2019 | Details | 1 pts |
| Halifax City White | 1 | @ | Highland FC | 13 | F | Feb 03, 2019 | Details | 3 pts |
| Halifax Dunbrack | 2 | @ | Highland FC | 5 | F | Feb 17, 2019 | Details | 3 pts |
| Highland FC | 3 | @ | Halifax City White | 0 | F | Feb 24, 2019 | Details | 3 pts |
| Highland FC | 9 | @ | Halifax City Green | 1 | F | Mar 02, 2019 | Details | 3 pts |
| United DFC | 4 | @ | Highland FC | 6 | F | Mar 10, 2019 | Details | 3 pts |