Rob Fleeting He was one of the best-known head football coaches in Connecticut high school football before stepping down as coach last summer.
On Thursday, it appeared the head coach-turned-assistant principal would be returning to Connecticut high school football.
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Rob Fleeting will return as the Flyers’ head football coach, according to an official social media announcement from Windsor Public Schools. Fleeting resigned as Windsor’s head coach in 2025, leaving the program to his son, Quinn.
We are excited for Coach Fleeting to continue to provide leadership in our school community and mentor our student-athletes as we enter the 2026-2027 season. Here’s to excellence in the classroom, strong character on campus, and continued success on the field.
The school began its search for a permanent head football coach as early as Dec. 23, 10 days after Windsor won the Class MM state championship. The younger Fleeting resigned on January 6.
Now, the elder Fleeting returns to coaching after compiling a 222-62-2 record with Windsor (2009-2024) and Weaver (1999-2009). Fleeting led Windsor to six state championship games and led the Flyers to a state title in 2014.
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Braves’ senior quarterback last season is a contender for 2025 Player of the Year Anthony RobinsonIn the 2025 season, he completed 197 of 302 passes for 3,647 yards, 50 touchdowns, and only 3 interceptions through the air.
Windsor is ranked No. 8 in Connecticut in the 2025 Massey High School Football Rankings.
About Windsor High School
Windsor High School is a dynamic public school committed to academic excellence and extracurricular growth. Windsor offers a rich, diverse curriculum and a range of sports and arts programs for students in grades 9 to 12. The Warriors excel in the classroom and on the court, fostering collaboration, leadership and pride within the community. The school encourages a well-rounded education to prepare students for future success in a global society.
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How to follow Connecticut high school football
For Connecticut high school football fans who want to keep up with scores from across the country, it’s now easier than ever to stay up to date with the Rivals High School Scoreboard. This comprehensive resource provides live updates and final scores throughout the Constitution State, ensuring you don’t miss out on Friday night’s action. From gripping games to spectacular performances, the Rivals High School Scoreboard is your one-stop destination for tracking all of Connecticut high school football action across the state.
