Share| Valley United | 2 | @ | South Shore | 2 | F | Nov 17, 2018 | Details | 1 pts |
| Halifax Dunbrack | 3 | @ | South Shore | 2 | F | Nov 24, 2018 | Details | 0 pts |
| Suburban FC | 3 | @ | South Shore | 3 | F | Dec 01, 2018 | Details | 1 pts |
| South Shore | 4 | @ | Suburban FC | 3 | F | Dec 08, 2018 | Details | 3 pts |
| South Shore | 2 | @ | United DFC | 7 | F | Dec 08, 2018 | Details | 0 pts |
| Halifax City (Forfeit) | 0 | @ | South Shore | 3 | F | Dec 22, 2018 | Details | 3 pts |
| United DFC | 5 | @ | South Shore | 5 | F | Jan 05, 2019 | Details | 1 pts |
| South Shore | 8 | @ | Halifax Dunbrack | 10 | F | Jan 12, 2019 | Details | 0 pts |
| South Shore | 5 | @ | Halifax City | 7 | F | Jan 12, 2019 | Details | 0 pts |
| Halifax County | 1 | @ | South Shore | 4 | F | Jan 19, 2019 | Details | 3 pts |
| South Shore | 6 | @ | Halifax County | 3 | F | Jan 26, 2019 | Details | 3 pts |
| South Shore | 3 | @ | Valley United | 2 | F | Feb 02, 2019 | Details | 3 pts |
| Halifax City | 3 | @ | South Shore | 4 | F | Feb 09, 2019 | Details | 3 pts |
| South Shore | 1 | @ | United DFC | 4 | F | Feb 23, 2019 | Details | 0 pts |
| South Shore | 4 | @ | Suburban FC | 4 | F | Feb 23, 2019 | Details | 1 pts |
| Halifax Dunbrack | 4 | @ | South Shore | 2 | F | Mar 02, 2019 | Details | 0 pts |
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