Windham heads to South Portland High School on Saturday, January 2, 2027. Since 2005-06, the Eagles are 5-15 against South Portland in the all-time series. The 2025-26 season saw Windham sweep the regular season series, winning 68-53 at home and 70-64 on the road in the most recent meeting on January 23, 2026. Windham has won the last 3 games against South Portland. The two teams also met in the 2024-25 playoffs, with Windham winning 55-52. Windham fans will see the two teams meet again as the new year begins.
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Windham at South Portland
Sat Jan 2 Away

Windham at South Portland
- First Team 10:00 AM
- Junior Varsity 11:30 AM
- Varsity 4:00 PM
South Portland HS
Preview
Recent meetings
Each game links to its source. Records from 2005–06 on (MaxPreps and the program’s own results).