The 2025 CIAC high school football playoffs are set. After a wild Thanksgiving week filled with upsets and last-minute drama, the 48 qualifying teams across six divisions now know their paths to a state title.
From New Britain edging out Fairfield Prep for the top spot in Class LL, to New Canaan and Darien lining up yet another rivalry showdown, this year’s bracket promises some of the most competitive postseason football Connecticut has seen in years.
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CIAC Playoff Format and Key Dates
The CIAC’s 2025 football playoffs feature a 48-team field divided into six classes: LL, L, MM, M, SS, and S. Each class sends eight teams into a standard bracket, with higher seeds hosting in the opening round.
The postseason gets underway on Tuesday at 6:30 p.m. with the quarterfinals. Winners advance to the semifinals on December 7, and state championships will be decided the weekend of December 12–13 at neutral sites around Connecticut, drawing fans from cities and towns like Hartford, New Haven, and Bridgeport.
How the Points System Shaped the Bracket
The CIAC point system shaped the seeding. Every win, opponent’s record, and strength-of-schedule detail mattered, especially at the top of Class LL, where fractions of a point separated the first and second seeds.
Class LL: New Britain Snags No. 1 Seed in Nail-Biter Finish
Kennedy’s 26–12 win over Crosby in Waterbury quietly reshaped the entire Class LL bracket. That outcome, combined with the existing point structure, allowed New Britain to edge out Fairfield Prep for the top seed by the razor-thin margin of 158.3 to 157.5 playoff points.
The New Britain Hurricanes now enjoy home-field advantage throughout the early rounds. That could draw packed crowds from surrounding communities like Berlin and Newington.
Class LL Quarterfinal Matchups
The Class LL bracket is loaded with power programs from across Connecticut’s football hotbeds. Fans in Stamford, Norwalk, and the wider Fairfield County corridor will see plenty of familiar faces:
Class L: New Canaan Leads the Pack, Darien Awaits
In Class L, the storyline almost writes itself. New Canaan enters the postseason at 10–0, the undisputed No. 1 seed after a flawless regular season built on disciplined defense and a balanced offense.
Their reward? A quarterfinal rematch with archrival Darien, seeded eighth. That matchup instantly becomes one of the most anticipated games in the state, especially for fans along the Gold Coast from Darien to nearby Stamford and Norwalk.
New Canaan vs. Darien: Rivalry Renewed
Few rivalries in Connecticut high school sports carry the intensity of New Canaan–Darien. The stakes are higher this time: win, and you’re two games from a championship; lose, and the season ends at the hands of your biggest rival.
Expect packed stands, tight coverage, and some emotional swings that define November and December football in this state.
Class MM and Class M: Windsor and St. Joseph on Top
In Class MM, the final playoff spot went down to the wire before the Plainfield/Quinebaug co-op clinched the No. 8 seed. Their reward is a tough road trip to face top-seeded Windsor, one of the state’s most consistent programs, drawing fans from across the greater Hartford and East Hartford area.
Class M features another powerhouse at the top: St. Joseph. After a dominant 35–0 win to end the regular season, St. Joseph locked down the No. 1 seed and will host Waterbury Career Academy in the quarterfinals.
Underdogs and Dark Horses
Windsor and St. Joseph come in as favorites. But co-op programs like Plainfield/Quinebaug and newer contenders such as Waterbury Career Academy bring some unpredictability.
One upset in these brackets could reshape the path to the title and give smaller communities—from Plainfield to parts of northeastern Connecticut—their moment in the spotlight.
Classes SS and S: Killingly and Woodland Lead the Smaller Schools
At the smaller-school level, tradition and toughness take center stage. Killingly secured the top seed in Class SS, continuing a run of strong seasons that have turned the program into one of the state’s model small-school programs.
In Class S, Woodland grabbed the No. 1 seed and will open against No. 8 Bloomfield. Bloomfield has a proud history and enough athleticism to cause problems for any top seed.
Rematches Highlight Competitive Balance
Several quarterfinals are rematches from the regular season, including Greenwich vs. Staples and New Canaan vs. Darien. Those repeat pairings just underscore what coaches have been saying for years: the competitive balance across Connecticut high school football, from New London to Bristol, has rarely been stronger.
What This Year’s Playoffs Mean for Connecticut Football
The 2025 CIAC playoff structure still rewards regular-season performance and keeps statewide representation in focus.
Powerhouses from big hubs like Hartford, New Haven, and Bridgeport get a shot alongside small-town teams from Killingly, Plainfield, and Woodland.
Quarterfinal night’s almost here. Communities from New Britain to Greenwich, Windsor to Waterbury—they’re all bracing for packed stadiums and cold bleachers.
It’s that kind of high-stakes football you only get in late fall around Connecticut. With six divisions, 48 teams, and a bunch of toss-up matchups, predicting who’ll make it to December feels impossible.
This year’s road to the championships? It’s bound to be intense, emotional, and honestly, probably unforgettable for everyone involved.
Here is the source article for this story: The CIAC high school football playoff schedule is set, but not before Thanksgiving upsets make impact
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