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Connecticut High School Football 2025 Playoff Brackets, Semifinal Schedule (CIAC) - December 8, 2025

Get every bracket and semifinal matchup in the 2025 Connecticut high school football playoffs
Robin Erickson|
New Canaan will face off against Windsor on Monday afternoon at 3:30 p.m. in a Class L semifinal matchup.
New Canaan will face off against Windsor on Monday afternoon at 3:30 p.m. in a Class L semifinal matchup. | Bill Berg

The 2025 Connecticut high school football playoffs continue on Monday, December 8 with 12 games in the semifinal round.

High School on SI has brackets for every classification and division in the Connecticut high school playoffs. The championship games will begin on December 13 at a location to be determined.

Connecticut High School Football 2025 Playoff Brackets, Semifinal Schedule (CIAC) - December 8, 2025

Class SS

Semifinals

Ledyard vs. Killingly - 12/08 at 3:30 p.m. EST

Nonnewaug vs. Hand - 12/08 at 6:30 p.m. EST

Class S

Semifinals

Sheehan vs. Woodland Regional - 12/08 at 5:00 p.m. EST

Northwest Catholic vs. Ansonia - 12/08 at 5:30 p.m. EST

Class MM

Semifinals

Newington vs. Windsor - 12/08 at 6:30 p.m. EST

Bunnell vs. Wilton - 12/08 at 4:30 p.m. EST

Class M

Semifinals

Brookfield vs. St. Joseph - 12/08 at 6:30 p.m. EST

Holy Cross vs. Berlin - 12/08 at 6:30 p.m. EST

Class LL

Semifinals

Southington vs. Norwich Free Academy - 12/08 at 5:00 p.m. EST

Greenwich vs. Fairfield Prep - 12/08 at 6:00 p.m. EST

Class L

Semifinals

Weaver vs. New Canaan - 12/08 at 3:30 p.m. EST

Cheshire vs. Ridgefield - 12/08 at 6:30 p.m. EST

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Robin Erickson
ROBIN ERICKSON

Robin Erickson has been covering high school sports since 2023 after graduating from Carroll College with a degree in Health Sciences. He began working in data operations at High School On SI before eventually going on to write articles for the company. A sports fan his entire life, Robin participated in soccer and basketball at the high school level, then committing to play soccer collegiately for Carroll. He currently lives in Boise with roommates who are equally in love with all things sports.