As the football season approaches we at GameTimeCT are breaking down the five best games from each CIAC conference.
Here are the 10 best games to watch in the Connecticut High School Football Alliance schedule for the 2023 season.
Dates and times can change throughout the season.
Masuk at Killingly, Sept. 8, 6:30 p.m.
Rematch of last year’s wild Class MM semifinal matchup won by Killingly in a 54-51 shootout. With Killingly getting bumped up to Class L, it won't have as big an impact on their respective playoff races, but an intriguing rematch, nonetheless.
Darien at North Haven, Sept. 8, 7 p.m.
Perennial title contenders face off for the third time in 10 seasons, but first since their back-to-back meetings in 2014 (both won by Darien). North Haven is coming off its first state championship. Darien, which missed the playoffs for the first time since 2012 is looking to get its mojo back under new coach Andy Grant.
West Haven at Staples, Sept. 8, 7 p.m.
These two proud programs broke minor Class LL playoff droughts only to see their strong seasons end ignominiously at home: West Haven to Glastonbury in a 17-7 outclass, and Staples to Fairfield Prep by a missed field goal attempt as time expired. Somebody's redemption tour can kick off here.
New Canaan at Shelton, Sept. 8, 7 p.m.
The perennially strong Gaels get first crack at the defending Class L champs and, perhaps, make their own play for the throne this year after falling a game short of facing the Rams in the Class L final.
Fairfield Prep at Greenwich, Sept. 9, 2 p.m.
These teams start 2023 the same way they ended 2022, just at Cardinals Stadium rather than Rentschler Field and without a trophy attached to it. This will be rematch of last year's Class LL championship game, won convincingly by Greenwich in a virtuoso defensive performance. Fortunately for Prep, Charlie Wilson (among others) will not be suited up this time. The game should be an early harbinger of what to expect from a pair of potential title contenders.
Killingly at Notre Dame-West Haven, Sept. 15, 7 p.m.
A Class MM runner-up, promoted now to Class L, visits last year's state champion in Class M, now moved up to Class LL. Both will look drastically different when they face off in this relatively intriguing bellwether showdown in Week 2. Killingly isn't getting a break after facing Masuk the week prior. Notre Dame gets St. Joseph after this. Good times.
Staples at Southington, Sept 22, 7 p.m.
Southington doesn't play two Alliance games like Staples must (wee). With the Wreckers having already played West Haven and Ridgefield by this point, this game likely makes or breaks its season. Southington.... not so much (qualifying is much easier than seasons prior). Still, a win here will go a long way.
Bloomfield at Masuk, Sept. 22, 7 p.m.
A fascinating matchup of two perennial playoff powerhouses. Bloomfield is hoping to finally break its run of state title losses in Class S. Masuk is looking to break through to its first final under coach Steve Christy. Bloomfield's Kerr Twins vs. Jason Champagne of Masuk.
Windsor at New Canaan, Sept. 23, 2 p.m.
These were perennial playoff foes back when we had four divisions. Turns out Windsor will remain in Class MM this year as it heads to always rough Dunning Field. We're not quite sure what defending L champion New Canaan will bring to the table. Windsor is looking to redeem itself after missing out on the postseason, even in a six-division getup.
Fairfield Prep at Darien, Sept. 23, 6 p.m.
Just in case their first Alliance matchups weren't tough enough, the schedule-makers bring this annual preseason scrimmage to life in the regular season. It's also a virtual rematch of the 2021 Class LL final, won by Darien.
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