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| All Schools |
| All Sports |
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| Baseball | | 4.24.2026 – Kennebunk 4, Portland 2 |
| 4.28.2026 – Biddeford 11, Portland 0 |
6:30 pm 4.30.2026 – Windham at Portland |
| 5.01.2026 – Windham 12, Portland 9 |
10 am 5.02.2026 – Falmouth at Portland |
| 5.04.2026 – Falmouth 3, Portland 2 |
| 5.05.2026 – Westbrook 5, Portland 2 |
| 5.07.2026 – South Portland 12, Portland 2 |
| 5.09.2026 – Sanford 13, Portland 0 |
| 5.12.2026 – Massabesic 6, Portland 5 |
4:30 pm 5.14.2026 – Thornton Academy at Portland |
| 5.16.2026 – Cheverus 21, Portland 2 |
4:30 pm 5.16.2026 – Cheverus at Portland |
| 5.18.2026 – Thornton Academy 8, Portland 0 |
| 5.19.2026 – Bonny Eagle 15, Portland 5 |
| 5.23.2026 – Gorham 13, Portland 3 |
| 5.26.2026 – Deering 4, Portland 2 |
| 5.28.2026 – Noble 8, Portland 5 |
10 am 5.30.2026 – Scarborough at Portland |
4:30 pm 6.02.2026 – Portland at Marshwood |
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