Windham High School established its football program in 1923 under the leadership of founding coach Tom Callaghan, with the team originally playing home games at Recreation Park in Willimantic, CT. The inaugural season was a success, as the Whippets posted an undefeated regular season with victories over historic conference foes New London, NFA, and Stonington, in addition to wins over Westerly (RI) and Hartford Public. For over a century, the Whippets have been a source of community pride and athletic excellence.
The 1923 Windham High School Football Team - Inaugural Undefeated Season
Just two years later in 1925, Coach Callaghan led the Whippets to another undefeated season. This remarkable team tied four games against Stonington, Chapman Tech (New London), Westerly, and Hartford Public, while securing decisive victories over Middletown, Wilby (Waterbury), Manchester, and Bristol Central. The 1925 team claimed a state championship and received votes in both the Hartford Courant and New Haven Register polls, though it was not considered a unanimous champion and is not officially recognized by the CIAC. Coach Callaghan's legacy as the founder of Windham football was later cemented with his induction into both the CHSCA Hall of Fame and the Windham Athletics Hall of Fame.
The 1925 Windham High School Football Team - Undefeated Season Under Coach Tom Callaghan
The 2023 Windham High School Football Team - 100 Years of Whippet Football
Windham holds a distinguished place in Connecticut high school football history as one of the founding members of the Eastern Connecticut Conference (ECC), alongside New London, Fitch, Norwich Free Academy, and Stonington. These conference rivalries have produced some of the most memorable games in program history.
From Recreation Park to Guild Field and now Ferrigno Field, generations of Whippets have worn the maroon and white with honor, continuing a tradition of toughness, dedication, and brotherhood that defines Windham Football.
Leadership that shaped Windham Football
Head Coach
Ed Ferrigno dedicated 38 years of his life to Windham High School as a teacher, coach, and athletic director. A 1943 graduate of Weaver-Hartford and UConn class of 1950, Ferrigno was a U.S. Army veteran of World War II who served in the European Theater and received the Silver Star for his bravery.
As head football coach from 1957 to 1984, Ferrigno compiled an impressive record of 148-113-6, building a program known for its toughness and discipline. He also served as Windham's athletic director from 1965 to 1994, shaping the entire athletics program for generations.
Perfect season as CCIL Champions. Before the modern CIAC playoff format, state champions were determined by state media polls—a testament to the dominance of Ferrigno's program.
"One thing about Ed Ferrigno is that he was very loyal to our association. He never said no to anything. Even after he retired, Ed was always doing things for the betterment of the organization."
— John Fontana, CHSCA Executive Director
Windham's home field, Ferrigno Field, is named in his honor, ensuring his legacy lives on with every game played under the Friday night lights.
Head Football Coach
A native of Warwick, Rhode Island and state wrestling champion at Bishop Hendricken High School, Brian Crudden graduated from Springfield College where he played football. He joined Windham High School as a teacher in the 1976-77 season and quickly became a pillar of the athletics program.
Crudden began his coaching career at Windham as an assistant coach before taking over the football program in 1985. For three decades, his dedication was legendary—from early August through late November, he poured his heart into building a competitive and disciplined football program. He would tell generations of athletes to "Respect All, Fear None" when preparing for a game, and often proclaimed that it was an ABNF—Absolutely Beautiful Night for Football.
Under Crudden's leadership, he compiled an impressive 172-149-3 record over 30 seasons. The Whippets qualified for the state playoffs five times—in 1992, 1996, 2005, 2006, and 2014—a remarkable achievement during an era when only four teams per division advanced to postseason play.
Crudden coached the team during a time when Windham competed in the CCC against tough opponents such as Hartford Public, Hall, Maloney, and Manchester. In his later years as a coach, he oversaw the transition of the program as it re-joined the ECC in the early 2000s to compete against historic rivals such as New London, NFA, Stonington, and Ledyard.
Class MM Championship Game
Windham was ranked #2 in Class MM and advanced to the title game against undefeated Newtown
Class M Championship Game
Perfect regular season record, advancing to the championship game against Hillhouse
"I have a high level of respect for him. As a coach, you knew Windham was always going to be prepared and was going to play to the final buzzer. But his success really goes back to family. He is such a family person both for his real family and his extended family — his football players. It's what he does, it's what he cares about. The players feel this and they buy in to what he's selling. He's as well a respected individual that I know."
— Coach Gene Blain, Killingly High School
Windham Football's playoff appearances under Coach Brian Crudden (1985-2015). Five playoff berths in an era when only four teams per division advanced to postseason play.
Throughout its playoff history, Windham has faced off against many of the state's most elite programs, testing the Whippets against Connecticut's best. Notable playoff matchups include Ansonia in 2014, New Canaan in the 1996 Class M semifinal, Daniel Hand in the 2005 Class M semifinal, and recent battles against Sheehan in 2023 and 2024. These matchups showcase Windham's ability to compete at the highest levels of Connecticut high school football.
A Legacy of Excellence - Celebrating 5 Perfect Regular Seasons in Windham Football History
Undefeated Regular Season
Undefeated Regular Season
Coach Tom Callaghan
Claimed State Championship
Undefeated Regular Season
Undefeated Regular Season
Received votes in Hartford Courant & New Haven Register polls
Undefeated Regular Season
Undefeated Season • Coach Tom Callaghan
Claimed State Championship (not officially recognized by CIAC)
Undefeated Regular Season Champions
5 Undefeated Regular Seasons - A Tradition of Excellence
*The 1925 team coached by Tom Callaghan claimed a state championship, though it is not officially recognized by the CIAC. The team tied 4 games that year against Stonington, Chapman Tech (New London), Westerly, and Hartford Public. Decisive wins against Middletown, Wilby (Waterbury), Manchester, and Bristol Central proved impressive. Tom Callaghan founded the program and was later elected into the CHSCA Hall of Fame and Windham Athletics Hall of Fame.
*The 1968 team received votes in the Hartford Courant and New Haven Register polls at season's end—the traditional method for determining state champions before the modern CIAC playoff system. While receiving recognition in these polls, this team is not considered an official state champion.