Here’s a look at the best matchups of Week 5 in CT high school football

We are entering Week 5 of the high school football season in Connecticut, and there are some interesting matchups on deck.

Southington and New Britain will square off in a CCC Tier 1 game Friday in New Britain. The Hurricanes beat Southington last year for the first time in 16 years, 28-25, and you can be sure the Knights are thinking about that game.

Cromwell/Portland will try to keep its unbeaten streak alive as it heads to Hartford for a game against the rejuvenated Weaver/Hartford Public/Classical co-op team.

Elsewhere, unbeaten Rockville (4-0) will face a test against the Somers/Stafford/East Windsor co-op (2-2). Windsor, also an unbeaten 4-0 and ranked 7th in the Courant’s state coaches’ poll, takes on Enfield (2-2).

Some of the best non-area matchups include No. 1 New Canaan traveling to Danbury (2-2), and No. 5 Staples traveling to No. 9 Wilton for an unbeaten FCIAC showdown.

Here are some of the games to watch this weekend:

Southington (2-2) at New Britain (3-1), Friday, 6 p.m.: Southington managed to pull off a last second win over Hall, 36-30, last week after losing two close ones in the waning moments of the game. The Knights will have their work cut out for them once again this week as they face red-hot New Britain, whose only loss came to Fairfield Prep, ranked ninth in the Courant state coaches poll, two weeks ago. Senior running back Jayden Allen has 773 yards and 13 touchdowns in four games for the Hurricanes.

Cromwell/Portland (4-0) at Weaver/Hartford Public/Classical (2-1), Friday, at Hartford Public, 7 p.m.: The Hartford co-op team will face one of its biggest tests of the season against unbeaten Cromwell/Portland. Cromwell’s senior quarterback Michael Sitaro Jr. has thrown eight touchdown passes and completed 23 of 37 attempts for 548 yards. He has also rushed for 337 yards and seven touchdowns. Senior Tyler Cipolla has 334 yards and five touchdowns for the Panthers. For Hartford, freshman Kadain Claflin-Coy has passed for five touchdowns while another freshman, Jameire Haughton, has rushed for 205 yards and two touchdowns.

Sheehan (3-1) at Xavier (1-3), Friday at 7 p.m.: Sheehan got its first SCC win last week against Amity and is looking for another one. Josh Durant (8 TDs, 489 rushing yards) had three touchdowns and Jake O’Brien had a passing touchdown and a rushing TD in the 35-13 win over Amity. Xavier coach Sean Marinan indicated in the early going that his team would be a work in progress this season and Xavier has lost one close game, 28-27, to Law and won a close one, 13-12 over NFA in overtime. And it doesn’t get any easier for the Falcons; after the Sheehan game, Xavier has to face Hand, No. 3 in the Courant’s state coaches’ poll, on Oct. 18.

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https://www.courant.com/2025/10/09/heres-a-look-at-the-best-matchups-of-week-5-in-ct-high-school-football/