New Canaan and Darien are set to face off in the Class L championship game, a matchup that feels inevitable at this point. After last Sunday’s semifinals, these two titans of Connecticut high school football are ready for a rematch—one that comes with a lot of heart.
New Canaan Handles Business Against Newtown
Let’s start with New Canaan’s win over Newtown. The Rams faced their toughest test since September but came through with a 35-20 victory. It was another showcase for Michael Smith, who turned in a “do-everything” performance. Two interceptions? Check. A blocked extra point to preserve the lead? Check. A late touchdown run to seal the deal? Why not?
On offense, Hudson Kenny set the tone early with a 59-yard touchdown run that left Newtown defenders chasing shadows. Meanwhile, Andrew Esposito continued his wizardry, scoring on the ground and hauling in a 19-yard touchdown pass from Luke Robinson. Robinson was his usual steady self—165 passing yards, two touchdowns, and no turnovers. If you’re looking for flash, Robinson isn’t your guy. If you’re looking for a quarterback who quietly wins games, look no further.
Newtown made it interesting, with quarterback Ryan Schoffstall throwing for 318 yards and keeping the Rams on edge in the first half. But New Canaan’s defense tightened up in the second half, forcing three turnovers and holding the Nighthawks to six points after halftime.
The Play by Play
First Quarter: Setting the Tone
Opening Drive: Newtown began with a long, methodical drive, converting multiple third downs. However, their momentum stalled in Rams territory when their field goal attempt was blocked by the New Canaan defense, with contributions from #97 Michael Harris and #15 Simon Tchakarov.
Kenny Strikes First: On New Canaan’s ensuing possession, #25 Hudson Kenny broke free for a spectacular 59-yard touchdown run, bursting through a well-constructed hole on the left side and outrunning the Newtown secondary. #8 Tucker Stevens added the extra point to make it 7-0.
Second Quarter: Trading Blows
Newtown Answers: Using a power-heavy set, Newtown’s Nick Pavia scored on a 5-yard run to tie the game at 7-7, capping off a balanced drive.
Cuesta Responds: Quarterback #12 Luke Robinson connected with #5 Chris Cuesta for a 23-yard touchdown on a precise throw over the middle, reclaiming the lead for New Canaan at 14-7 after another Stevens PAT.
Pavia Again: Not to be outdone, Newtown leaned on their ground game again, with Pavia punching it in from 2 yards out to tie the game at 14-14 just before halftime.
Third Quarter: Adjustments Pay Off
Esposito in the Wildcat: New Canaan’s first drive of the second half set the tone, with #14 Andrew Esposito taking a 2-yard Wildcat run into the end zone. The scoring drive was set up by a key 30-yard pass from Robinson to Esposito.
Taylor’s Spark, but Smith Shines: Newtown’s Ryan Schoffstall hit Jayden Taylor on a short pass, which Taylor turned into a 63-yard touchdown thanks to a dazzling display of speed and elusiveness. However, #7 Michael Smith blocked the extra point, preserving New Canaan’s slim 21-20 lead.
Esposito Strikes Again: Robinson found Esposito on a 19-yard touchdown pass, extending the Rams’ lead to 28-20.
Fourth Quarter: Sealing the Deal
Smith Closes It Out: #7 Michael Smith capped off his heroic performance with a 4-yard touchdown run late in the quarter, giving New Canaan an insurmountable 35-20 lead.
Defensive Stand: Newtown made a final push, but Schoffstall, under constant pressure from #15 Simon Tchakarov and #97 Michael Harris, threw his third interception of the day, this time to #6 Mikey Hiraman.
Darien Overcomes a Slow Start
While New Canaan was pulling away from Newtown, Darien was busy shaking off an ugly start against Notre Dame-West Haven. After fumbling the opening kickoff and falling behind early, the Blue Wave turned to quarterback Ben Rolapp, who delivered one of his best performances of the season. Four touchdown passes and a rushing score later, Darien had a 35-21 win and a ticket to the championship.
Darien’s second-half adjustments were the difference. Rolapp found his rhythm, connecting with Charles Thom for two touchdowns, including a highlight-reel 36-yarder that showcased Thom’s mix of size, strength, and speed. Thom, who had struggled in the Turkey Bowl against New Canaan, looked like a completely different player on Sunday.
Head coach Andy Grant attributed the win to halftime adjustments and the team’s conditioning. Darien’s ability to wear down Notre Dame-West Haven’s two-way players paid dividends, as the Blue Wave dominated the second half on both sides of the ball.
The Rivalry Renewed
Now, the focus shifts to Saturday’s championship game at Central Connecticut State University. It’s the third meeting between New Canaan and Darien in the last four years, and the stakes couldn’t be higher. New Canaan is chasing a three-peat and its 15th state title. Darien, meanwhile, is seeking revenge after a 34-0 Thanksgiving loss that still stings.
New Canaan has owned this rivalry recently, winning eight of the last nine matchups. Their defense, led by Smith and Simon Tchakarov, has been dominant all season, allowing just 9.8 points per game. Offensively, Robinson, Kenny, and Esposito form a trio that can grind out drives or hit big plays when needed.
But Darien isn’t going down without a fight. Rolapp is playing with confidence, and Thom looks like he’s finally hitting his stride. If the Blue Wave can limit turnovers and control the clock, this could be the kind of back-and-forth battle fans dream about.
Final Thoughts
This is what high school football is all about—two great teams, a heated rivalry, and a championship on the line. For New Canaan, it’s a chance to cement their legacy. For Darien, it’s an opportunity to rewrite the narrative.
Mark your calendars. This one’s going to be a classic.
