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| All Schools |
| All Sports |
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| Basketball - Boys | | 12.12.2023 – Shead 59, Woodland 41 |
| 12.14.2023 – Machias 53, Woodland 52 |
| 12.19.2023 – Jonesport-Beals 77, Woodland 52 |
| 12.23.2023 – Mattanawcook Academy 51, Woodland 46 |
| 12.28.2023 – George Stevens 83, Woodland 37 |
| 1.02.2024 – Woodland 69, Shead 29 |
| 1.04.2024 – Washington Academy 55, Woodland 34 |
| 1.06.2024 – Penobscot Valley 63, Woodland 51 |
| 1.11.2024 – Calais 84, Woodland 40 |
| 1.12.2024 – George Stevens 77, Woodland 48 |
1:30 pm 1.13.2024 – George Stevens at Woodland |
6:30 pm 1.16.2024 – Machias at Woodland |
1:30 pm 1.20.2024 – Woodland at Mattanawcook Academy |
6:30 pm 1.23.2024 – Woodland at Narraguagus |
6:30 pm 1.25.2024 – Jonesport-Beals at Woodland |
1:30 pm 1.27.2024 – Narraguagus at Woodland |
6:30 pm 1.30.2024 – Woodland at Washington Academy |
1:30 pm 2.03.2024 – Penobscot Valley at Woodland |
6:30 pm 2.06.2024 – Woodland at Calais |
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