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| All Schools |
| All Sports |
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| Softball | | 4.28.2026 – Vinalhaven 20, Boothbay/Wiscasset 0 |
| 4.28.2026 – Forest Hills 20, Boothbay/Wiscasset 2 |
4 pm 4.30.2026 – Boothbay/Wiscasset at Valley |
| 5.04.2026 – Richmond 20, Boothbay/Wiscasset 5 |
4 pm 5.06.2026 – Temple at Boothbay/Wiscasset |
3:30 pm 5.08.2026 – Boothbay/Wiscasset at Greenville |
| 5.11.2026 – Temple 15, Boothbay/Wiscasset 5 |
| 5.11.2026 – Temple 7, Boothbay/Wiscasset 4 |
| 5.13.2026 – Rangeley 12, Boothbay/Wiscasset 1 |
| 5.13.2026 – Rangeley 13, Boothbay/Wiscasset 3 |
3:30 pm 5.15.2026 – Greenville at Boothbay/Wiscasset |
| 5.19.2026 – Telstar/Gould 20, Boothbay/Wiscasset 3 |
| 5.20.2026 – Valley 17, Boothbay/Wiscasset 1 |
11 am 5.26.2026 – Boothbay/Wiscasset at Vinalhaven |
| 5.27.2026 – Buckfield 18, Boothbay/Wiscasset 3 |
9:30 am 5.30.2026 – Greenville at Boothbay/Wiscasset |
| 6.02.2026 – Richmond 22, Boothbay/Wiscasset 1 |
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