Rob Fleeting was one of Connecticut high school football’s most well known names when it came to head football coaches before he stepped away from coaching last summer.

On Thursday, it looks like the head coach-turned-assistant principal is returning to coach Connecticut high school football one more time.

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According to an official social media announcement by Windsor Public Schools, Rob Fleeting is returning to become the head football coach of the Flyers. Fleeting had stepped down as Windsor’s head coach in 2025, leaving the program to his son, Quinn.

We are excited to have Coach Fleeting continue his leadership in our school community and guide 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 had initially opened up a coaching search for a permanent head football coach back on Dec. 23, 10 days after Windsor had won the Class MM state title. The younger Fleeting put in his resignation on Jan. 6.

Now the older Fleeting returns to the coaching saddle after putting together a 222-62-2 record between his stints at Windsor (2009-2024) and Weaver (1999-2009). Fleeting led Windsor to the state championship game six times, leading the Flyers to the state title win in 2014.

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The Warriors last season featured the Rivals 2025 Player of the Year in senior quarterback Anthony Robinson, who finished the 2025 season completing 197 of 302 passes for 3,647 yards, 50 touchdowns and only three interceptions through the air.

Windsor finished as the No. 8 ranked team per the Connecticut 2025 High School Football Massey Rankings.

More about Windsor High School

Windsor High School is a dynamic public school dedicated to academic excellence and extracurricular growth. Serving students from grades 9-12, Windsor provides a rich, diverse curriculum paired with an array of athletic and arts programs. The Warriors excel both in the classroom and on the field, fostering a spirit of collaboration, leadership, and pride within the community. The school encourages a well-rounded education, preparing 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 looking to keep up with scores around the nation, staying updated on the action is now easier than ever with the Rivals High School Scoreboard. This comprehensive resource provides real-time updates and final scores from across the Constitution State, ensuring you never miss a moment of the Friday night frenzy. From nail-biting finishes to dominant performances, the Rivals High School Scoreboard is your one-stop destination for tracking all the Connecticut high school football excitement across the state.