| Suburban FC | 10 | @ | Highland FC | 4 | F | Nov 04, 2018 | Details | 0 pts |
| Highland FC | 1 | @ | Halifax Dunbrack | 4 | F | Nov 11, 2018 | Details | 0 pts |
| Halifax City | 1 | @ | Highland FC | 0 | F | Nov 18, 2018 | Details | 0 pts |
| United DFC | 7 | @ | Highland FC | 1 | F | Nov 25, 2018 | Details | 0 pts |
| Halifax County Tigers | 0 | @ | Highland FC | 1 | F | Dec 02, 2018 | Details | 3 pts |
| Highland FC | 1 | @ | Halifax County Saints | 6 | F | Dec 16, 2018 | Details | 0 pts |
| Highland FC (Forfeit) | 0 | @ | United DFC | 3 | F | Dec 23, 2018 | Details | 0 pts |
| Halifax County Saints | 4 | @ | Highland FC | 1 | F | Jan 13, 2019 | Details | 0 pts |
| Highland FC (Forfeit) | 0 | @ | Halifax City | 3 | F | Jan 27, 2019 | Details | 0 pts |
| Suburban FC | 2 | @ | Highland FC | 1 | F | Feb 03, 2019 | Details | 0 pts |
| Halifax City | 5 | @ | Highland FC | 1 | F | Feb 10, 2019 | Details | 0 pts |
| Highland FC | 2 | @ | Halifax County Tigers | 2 | F | Feb 23, 2019 | Details | 1 pts |
| Halifax Dunbrack | 8 | @ | Highland FC | 2 | F | Mar 10, 2019 | Details | 0 pts |