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From Thanksgiving Rivalries to a 36-Game Win Streak The Legacy of Cheshire High School Football

  • Writer: Richard Smith
    Richard Smith
  • Nov 26, 2025
  • 3 min read

Updated: Dec 28, 2025

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Cheshire High School football has a rich history marked by intense rivalries and remarkable achievements. From early struggles to a dominant era in the 1990s, the Rams have built a legacy that continues to inspire players and fans alike. This story highlights the evolution of Cheshire’s football program, focusing on its traditional Thanksgiving rivalries and the unforgettable 36-game winning streak that defined a generation.


Early History and Thanksgiving Rivalries


Cheshire High School’s football program began to take shape in the mid-1950s after the school was built. The early years were challenging. For example, in the 1962 season, the team faced a tough stretch where they lost all six games at one point. Despite these setbacks, the program laid the foundation for future success.


A key part of Cheshire’s early football identity was its Thanksgiving Day rivalry with Lyman Hall High School in Wallingford. This annual game was more than just a contest; it was a community event that drew large crowds regardless of weather conditions. One memorable instance occurred in 1962 when heavy rain forced the postponement of the game to the following day, showing how important the matchup was to both towns.


Other notable opponents during this period included Derby High School. Cheshire played Derby in 1962 and again during the 1990s winning streak, adding to the competitive spirit that fueled the team’s growth.

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The Dominant 1990s Era


The 1990s marked the golden age of Cheshire High School football. The Rams set a state record with a 36-game winning streak spanning from 1991 to 1996. This impressive run included four consecutive state championships in Class L from 1992 through 1995, a feat that solidified Cheshire’s place in Connecticut high school football history.


During this period, Cheshire faced tough competition from schools such as North Haven, Sheehan, Derby, Amity, Shelton, and Southington. Each game tested the Rams’ resilience and skill, but the team consistently rose to the challenge. The streak showcased not only the talent on the field but also the strength of the coaching staff and the support from the community.


The 1990s success brought pride to Cheshire and created lasting memories for players and fans. The team’s ability to maintain focus and perform under pressure remains a benchmark for future Rams squads.

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The Current Rivalry and the Apple Valley Classic


Today, Cheshire’s Thanksgiving tradition continues with a new rivalry against Southington High School in the annual Apple Valley Classic. This game has become a highlight of the season for both teams, often carrying playoff implications that add to the excitement.


In 2023, Cheshire broke a long losing streak against Southington with a 34-20 victory, reigniting the competitive spirit between the schools. The Apple Valley Classic has grown into a celebrated event that honors the history of Thanksgiving football while looking forward to new chapters in the rivalry.


The matchup between Cheshire and Southington reflects the passion and dedication that define high school football in the region. Fans eagerly anticipate this game each year, knowing it represents more than just a contest—it’s a continuation of tradition and community pride.



Summary


Cheshire High School football has evolved from early struggles to a powerhouse program with a record-setting 36-game winning streak and multiple state championships. The Thanksgiving rivalries, first with Lyman Hall and now with Southington in the Apple Valley Classic, have been central to the team’s identity and community spirit.


The legacy of Cheshire football is built on resilience, tradition, and a commitment to excellence. As the Rams continue to face new challenges and rivalries, they carry forward a proud history that inspires players and fans every season.


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