| All Schools |
| |
| Soccer - Boys |
| 9.07.2023 – Woodland 3, Jonesport-Beals 2 |
| 9.11.2023 – Narraguagus 5, Woodland 0 |
| 9.13.2023 – Lee Academy 7, Woodland 2 |
| 9.18.2023 – Sumner 4, Woodland 0 |
| 9.20.2023 – Lee Academy 5, Woodland 3 |
| 9.25.2023 – MSSM 3, Woodland 2 |
| 9.27.2023 – Woodland 2, Sumner 2 |
| 9.29.2023 – Woodland 2, Machias 1 |
| 10.03.2023 – Woodland 2, Jonesport-Beals 1 |
| 10.05.2023 – Calais 6, Woodland 0 |
| 10.12.2023 – Narraguagus 2, Woodland 0 |
| 10.14.2023 – Woodland 3, Washburn 0 |
| 10.16.2023 – Calais 0, Woodland 0 |
| 10.20.2023 – Katahdin 1, Woodland 0 |
| |
| Soccer - Girls |
| 9.06.2023 – Woodland 12, East Grand 0 |
| 9.08.2023 – Mattanawcook Academy 7, Woodland 0 |
| 9.13.2023 – Woodland 4, Calais 1 |
| 9.21.2023 – Woodland 2, Shead 1 |
| 9.23.2023 – Bangor Christian 3, Woodland 1 |
| 9.25.2023 – Woodland 5, Narraguagus 0 |
| 9.29.2023 – Penobscot Valley 10, Woodland 0 |
| 10.02.2023 – Woodland 8, East Grand 0 |
| 10.05.2023 – Shead 2, Woodland 1 |
| 10.06.2023 – Bangor Christian 3, Woodland 0 |
| 10.11.2023 – Woodland 3, Narraguagus 0 |
| 10.14.2023 – Central Aroostook 10, Woodland 0 |
| 10.17.2023 – Woodland 4, Calais 0 |
| 10.20.2023 – Fort Fairfield 3, Woodland 2 |
