All schedules are not created equal. Which CT football teams will be helped, hurt most by theirs.

Cheshire's #10 Aiden Gregorich rushes for yardage as Sheehan's #58 Mason Johnson pursues during a CIAC high school football game at Cheshire High School in Cheshire, Conn., Friday, November 7, 2025. (Dave Zajac/Hearst Connecticut Media)

With six high school football playoff divisions in the CIAC , the margin between reaching the postseason and being left out can be razor thin.

Sometimes, that margin starts with the schedule.

Over the years, we've seen very good teams draw difficult slates, finish around .500 and wind up on the outside of the CIAC playoffs. We've also seen teams benefit from more manageable schedules that provide a greater margin for error.

That doesn't mean a playoff berth is handed to anyone. It just means some roads are considerably tougher than others.

Not all schedules are created equally, so GametimeCT's Will Aldam and Pete Paguaga took a look at five teams that could be hurt by difficult schedules and five that should benefit from more favorable ones.

Five teams who could be hurt by schedule

Cheshire

2025 Record: 9-4

Should win:

Guilford

Could win:

West Haven, Glastonbury, Notre Dame-West Haven, Staples, Jonathan Law, Sheehan

Toss-up:

Hand, Fairfield Prep, Southington

Cheshire reached the CIAC Class L championship game and fell to New Canaan 34-13. The Rams return a number of starters from last year's run, but graduated All-State QB/LB Aiden Gregorich and now face one of the most difficult schedules in the state. Its opponents had a combined record of 80-36 (.690) last year, and the group includes two defending state champions, a runner-up and a semifinalist. Nine of Cheshire's 10 opponents reached the playoffs last year.

Enfield

2025 Record: 6-4

Should win:

Manchester, South Windsor

Could win:

Hall, Maloney

Toss-up:

Fairfield Ludlowe, Glastonbury, New Britain, Southington, Berlin, Windsor

Enfield finished just 25 power points out of a 2025 Class L playoff berth at 6-4. Now the Eagles move up to Tier 1 of the CCC this year, which means a tougher schedule that includes six opponents who reached the CIAC playoffs last year, including two defending state champions and a runner-up. Enfield is set up well with its 11 returning starters, including All-Conference quarterback Sawyer Pequita and two-time All-State lineman Joel Budd. Enfield's 2026 season will certainly be one to follow.

Glastonbury

2025 Record: 7-4

Should win:

Manchester, Conard, Simsbury

Could win:

Maloney, Enfield

Toss-up:

Cheshire, St. Joseph, New Britain, Southington, Windsor

Glastonbury reached the CIAC Class LL quarterfinals last year  before falling to Southington 35-30. Glastonbury returns star running back Dante Casdia, but graduated several other starters. The Guardians have one of the toughest schedules in the state this year. Five opponents reached the postseason last year, a group that includes a defending state champion, two runners-up and a semifinalist.

For a team replacing significant experience, that's not exactly a gentle runway back to the playoffs.

West Haven

2025 Record: 5-5

Should win:

Norwalk, Guilford

Could win:  Jonathan Law, Ludlowe, North Haven

Toss-up: Cheshire, Sheehan, Hand, Fairfield Prep, New Britain

West Haven narrowly missed out on the Class LL tournament last year after reaching back-to-back state finals. A difficult schedule won't make it any easier. The Blue Devils' 2026 opponents went a combined 84-31 last season, a .730 winning percentage. Eight reached the postseason, including two defending state champions, a state runner-up and a semifinalist. West Haven also has to replace significant production at quarterback and running back as coach Tom Unger enters his second season.

Wilton

2025 Record:

10-2

Should win:

Norwalk, Westhill, Stamford

Could win:

Staples, Ridgefield

Toss-up:

Berlin, Southington, St. Joseph, Greenwich, New Canaan

Wilton is coming off a terrific season that ended in the CIAC Class MM semifinals. The Warriors graduated quarterback Charlie Calabrese and three of his top receivers, but star running back Dennis Dustin returns. The bigger concern may be a schedule that gets progressively more difficult. Seven opponents reached the postseason last year, and early November brings back-to-back games against four-time defending Class L champion New Canaan and two-time defending Class LL champion Greenwich. Then again, Wilton has beaten Greenwich in each of the past two seasons.

- Will Aldam

Five Teams Helped by Schedule

Lyman Hall

2025 Record: 7-3

Should win: Ledyard, New Milford, Hillhouse, East Haven

Could win: Branford, Hamden

Toss-up: Sheehan

Lyman Hall carries a lot of memories from last season. The Trojans just missed out on a state playoff berth and it wasn't because they didn't win enough games. They won seven. But their schedule didn't help their point total and they were faced with a win-and-in scenario on Thanksgiving morning, a game they lost to Sheehan. Once again, the Trojans schedule doesn't look daunting to start, with just two playoff teams (Ledyard and Guilford) in the first seven games. All seven of those games could/should be won by the Trojans, who bring back a bunch of talent led by quarterback Ryan Casey. There is a very real path to another seven-win season before the schedule gets challenging, with games against Hand, Law and Sheehan, teams they are a combined 10-31 against since 2004. They will likely need to beat one of them to get in. Good luck Trojans.

Newtown

2025 Record: 8-3

Should win:

New Fairfield, Pomperaug, Notre Dame-Prep, Joel Barlow, New Milford, Brookfield, Masuk

Could win: Southington

Toss-up: Bunnell

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