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| All Schools |
| All Sports |
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| Softball | 4:30 pm 4.10.2026 – Portland/Deering at Wells |
4:30 pm 4.13.2026 – Poland Regional at Portland/Deering |
4:30 pm 4.14.2026 – Poland Regional at Portland/Deering |
| 4.24.2026 – South Portland 21, Portland/Deering 0 |
| 4.27.2026 – Thornton Academy 15, Portland/Deering 0 |
| 4.29.2026 – Westbrook 19, Portland/Deering 1 |
| 5.01.2026 – Biddeford 15, Portland/Deering 0 |
| 5.04.2026 – Bonny Eagle 11, Portland/Deering 0 |
4:30 pm 5.06.2026 – Portland/Deering at Cheverus |
| 5.08.2026 – Windham 18, Portland/Deering 2 |
| 5.13.2026 – Gorham 15, Portland/Deering 6 |
5 pm 5.15.2026 – Kennebunk at Portland/Deering |
| 5.16.2026 – Kennebunk 15, Portland/Deering 4 |
| 5.18.2026 – MBAT 12, Portland/Deering 0 |
| 5.20.2026 – Portland/Deering 12, Massabesic 10 |
4:30 pm 5.21.2026 – Portland/Deering at Cheverus |
| 5.22.2026 – Portland/Deering 12, Noble 11 |
| 5.26.2026 – Sanford 6, Portland/Deering 5 |
| 5.28.2026 – Scarborough 15, Portland/Deering 2 |
| 6.02.2026 – South Portland 15, Portland/Deering 0 |
| 6.04.2026 – Westbrook 15, Portland/Deering 0 |
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