The 2026 high school football season is shaping up as a rigorous test for the six programs that captured CIAC titles in 2025. Each champion now faces a slate that blends traditional rivals with a new wave of playoff-caliber opponents, raising the stakes for another repeat run.
A crowded road to repeat
Greenwich, which has claimed three of the last four Class LL crowns, opens its schedule with a showdown against New Canaan, the reigning Class L favorite. Senior quarterback Lucca Boyce will anchor an offense that must navigate seven playoff teams from a year ago, including a late‑season clash with New Canaan on Oct. 23 that could decide the league’s ultimate narrative.
New Canaan, the four‑time champion, is slated for a marquee Alliance game against Fairfield Prep and a rematch with Greenwich later in the year. Defensive stalwart Paul Fumex returns to lead a unit that will also meet Wilton, Ludlowe and Darien in the second half, setting up a potential Thanksgiving showdown that could seal another title.
Windsor, the defending Class MM champion, must replace GametimeCT Player of the Year AJ Robinson, whose graduation leaves a void in the backfield. Early tests against New Britain and St. Joseph, both playoff teams in 2025, will gauge whether the team can sustain its momentum.
Berlin, fresh from its first state championship since 2009, will compete in Class SS next season. The Bears are slated to meet perennial powers Hand, Killingly and Ansonia, a move that could reshape the competitive balance in the division.
Hand, the 2025 Class SS champion, faces a demanding schedule that includes five games against CIAC playoff teams, highlighted by a revenge match against Cheshire. The squad’s road trip begins in Rhode Island, adding a geographic twist to its campaign.
Sheehan, which captured Class S in 2025, enters the new season with the highest winning percentage (.679) among the defending champions. Rising star Eli Rice is expected to play a pivotal role as the team confronts a tough slate of opponents.
The expanded playoff landscape
The CIAC’s expansion to six football divisions in 2022 has distributed 24 titles among 15 schools, a milestone that underscores the growing depth of competition. As the new schedules unfold, the convergence of experience, talent and challenging matchups promises a season that could rewrite the narrative of repeat champions.