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| All Schools |
| All Sports |
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| Soccer - Boys | | 9.05.2023 – Calais 1, Narraguagus 1 |
| 9.07.2023 – Washington Academy 7, Calais 2 |
| 9.12.2023 – Calais 5, Shead 2 |
| 9.19.2023 – Calais 4, Machias 2 |
| 9.20.2023 – Narraguagus 3, Calais 1 |
| 9.23.2023 – Mattanawcook Academy 2, Calais 2 |
| 9.26.2023 – Calais 3, Jonesport-Beals 2 |
| 9.28.2023 – Washington Academy 8, Calais 1 |
| 10.03.2023 – Calais 3, Mattanawcook Academy 2 |
| 10.05.2023 – Calais 6, Woodland 0 |
| 10.10.2023 – Jonesport-Beals 1, Calais 1 |
| 10.12.2023 – Calais 6, Shead 1 |
| 10.13.2023 – Calais 2, Machias 0 |
| 10.16.2023 – Calais 0, Woodland 0 |
| 10.25.2023 – Fort Kent 6, Calais 1 |
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