| Halifax County | 0 | @ | Highland FC | 0 | F | Nov 11, 2018 | Details | 1 pts |
| Highland FC | 2 | @ | Halifax Dunbrack Red | 8 | F | Nov 17, 2018 | Details | 0 pts |
| Suburban FC | 4 | @ | Highland FC | 0 | F | Nov 25, 2018 | Details | 0 pts |
| Highland FC | 0 | @ | United DFC Electric | 3 | F | Dec 01, 2018 | Details | 0 pts |
| Highland FC | 0 | @ | United DFC Navy | 1 | F | Dec 08, 2018 | Details | 0 pts |
| Halifax Dunbrack Red | 6 | @ | Highland FC | 0 | F | Dec 16, 2018 | Details | 0 pts |
| Highland FC | 2 | @ | Halifax City | 2 | F | Dec 22, 2018 | Details | 1 pts |
| Highland FC | 0 | @ | Valley United | 8 | F | Jan 05, 2019 | Details | 0 pts |
| Cape Breton | 0 | @ | Highland FC | 5 | F | Jan 13, 2019 | Details | 3 pts |
| Highland FC | 0 | @ | Halifax Dunbrack Black | 1 | F | Jan 26, 2019 | Details | 0 pts |
| Highland FC | 1 | @ | Suburban FC | 3 | F | Jan 27, 2019 | Details | 0 pts |
| United DFC Navy | 5 | @ | Highland FC | 1 | F | Feb 10, 2019 | Details | 0 pts |
| Highland FC | 0 | @ | Cape Breton | 1 | F | Feb 16, 2019 | Details | 0 pts |
| Halifax Dunbrack Black | 1 | @ | Highland FC | 3 | F | Feb 24, 2019 | Details | 3 pts |