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| All Schools |
| All Sports |
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| Ice Hockey | | 12.07.2019 – Saint Dominic 4, SPortland/Freeport/Waynflete
3 |
| 12.12.2019 – SPortland/Freeport/Waynflete
5, Portland/Deering 0 |
| 12.14.2019 – SPortland/Freeport/Waynflete
3, Bangor 0 |
| 12.19.2019 – SPortland/Freeport/Waynflete
3, Yarmouth 0 |
| 12.21.2019 – Biddeford/Massabesic/OOB 1, SPortland/Freeport/Waynflete
1 |
| 12.30.2019 – Scarborough 6, SPortland/Freeport/Waynflete
2 |
| 1.09.2020 – SPortland/Freeport/Waynflete
3, Cape Elizabeth 2 |
| 1.15.2020 – SPortland/Freeport/Waynflete
3, Saint Dominic 0 |
| 1.18.2020 – Lewiston 2, SPortland/Freeport/Waynflete
0 |
| 1.23.2020 – SPortland/Freeport/Waynflete
2, Biddeford/Massabesic/OOB 1 |
| 1.25.2020 – Bangor 6, SPortland/Freeport/Waynflete
5 |
| 1.28.2020 – SPortland/Freeport/Waynflete
5, Windham/Westbrook/Bonny Eagle 2 |
| 2.01.2020 – SPortland/Freeport/Waynflete
6, Marshwood/Traip/Sanford/Noble 1 |
| 2.05.2020 – Edward Little 3, SPortland/Freeport/Waynflete
2 |
| 2.08.2020 – SPortland/Freeport/Waynflete
6, Fryeburg/Lakes Region 2 |
| 2.13.2020 – Thornton Academy 2, SPortland/Freeport/Waynflete
0 |
| 2.15.2020 – SPortland/Freeport/Waynflete
6, Portland/Deering 1 |
| 2.18.2020 – SPortland/Freeport/Waynflete
4, Falmouth 3 |
| 3.03.2020 – Lewiston 5, SPortland/Freeport/Waynflete
1 |
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