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
Newtown, Newtown, Newtown the Alliance can't do all of the work for you. This is not meant as a knock on the SWC at all, but you have to wonder if Newtown has outgrown the rest of the league. Over the last five seasons, Newtown has lost 13 games, only two of those have come to an SWC team, both Masuk. With eight SWC games on the schedule and Alliance games against Southington and Greenwich, there is a realistic path to eight wins, potentially nine.
Rocky Hill- 2025 Record:5-5
- Should win: Tolland, Cheney/Windham Tech, RHAM, Lewis Mills/Wolcott Tech, East Catholic, Avon/St. Paul
- Could win:Middletown, Northwest Catholic, Plainville
- Toss-up: Cromwell/Portland
The Terriers took big strides last year to get to 5-5 with a young group and look to take a step forward this season. With a schedule like theirs, a step forward is very realistic. Over the past five seasons, Rocky Hill has losing records against Northwest Catholic (2-3), Plainville (0-2), RHAM (0-1) and Cromwell/Portland (0-5). The Terriers have winning records against five other teams on this year's schedule and have not faced Cheney/Windham Tech during that span. Led by Tyshawn Dominique and quarterback Mason Margiotta, Rocky Hill has a legitimate chance to pile up wins before the annual Shunpike Showdown against Cromwell/Portland.
Trumbull- 2025 Record:3-7
- Should win: Crosby, Norwalk, Danbury, McMahon, Warde
- Could win:Shelton, Ridgefield
- Toss-up:Ludlowe
The Golden Eagles are pumped for this season and after looking at their schedule, they should be excited. Only two of the FCIAC's traditional heavyweights, New Canaan and St. Joseph, appear on the slate, and those games bookend Trumbull's season. Their Alliance games are against Crosby of the NVL and Shelton of the SCC. The Gaels have also fallen on tough times. Against its six FCIAC opponents not named New Canaan or St. Joseph, Trumbull has gone a combined 14-1 over the past five seasons. That figure does not include Norwalk, which the Golden Eagles haven't faced since 2019. Trumbull has a lot to fix after a 3-7 season, but after its opener against New Canaan, the Eagles should be in cruise control until November when they get Fairfield Ludlowe and St. Joseph in two of the final three games.
Torrington- 2025 Record: 7-4
- Should win: Kennedy, Crosby, Oxford, Wilby, Wolcott, Watertown
- Could win: Fitch, GNH
- Toss-up:Naugatuck
The Naugatuck Valley League finally joined the Alliance to help their teams better prepare for the state playoffs, but still the league scheduling still doesn't make sense. The league adopted a power scheduling model and some teams reap the benefits. Almost every year, Torrington seems to be one of them. Just two of its opponents had winning records last year: NVL power Ansonia, which is 13-0 against Torrington since 2004, and Fitch of the Eastern Connecticut Conference. Against eight of its other 2026 opponents last season, Torrington went 7-1 and outscored them 334-115. The Raiders scored at least 39 points in each of those seven victories. Their lone loss in that group was a 20-16 game against Naugatuck. Torrington is looking at eight to nine wins this season.
- Pete Paguaga
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