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10. CHRIS WEBSTER (North Branford). program at on the Connecticut map. She guided the school to its first-ever state championship in 1976. In the 1986-87 season, North Branford was perfect, going 26-0 en route to another state championship. Webster, who is a member the Connecticut Women's Basketball Hall of Fame, has coached for more than 30 years, winning more than 400 games and a total of four state titles.
9. GUY WHITTEN (Wilton) Whitten was the varsity football coach when he was asked by the administration at in 1969, to start a lacrosse program from scratch. Whitten built the program into a juggernaut, helping the Warriors win 17 state titles in his 26 years as the head coach. Whitten retired in 1995 with a spectacular record of 410-77 for a winning percentage of .842. Known as one of the founding fathers for Connecticut lacrosse.
8. ED ASTON (Cheshire). Aston spent 37 years as the swim coach for the boys and girls teams at . During that time, Aston racked up more than (boys and girls), and 14 State Open championships. He coached more than 100 All-Americans and is a member of the National Coach of the Year Hall of Fame.
7. JACKIE DINARDO (Danbury) A former standout basketball player at the University of Texas, Dinardo is a member of the Texas Hall of Fame. She has been the girls for the last 26 years, leading the Hatters to more than 400 wins . In her dual roles as basketball and volleyball coach, Dinard had helped capture 25 league titles. She will be inducted into the Connecticut Women's Coaches Hall of Fame on April 11 in Hamden.
6. MICKEY LIONE, Jr. (Stamford) 27 of them at Stamford Catholic (now ). Lione coached baseball from 1971-1998 and hockey from 1979-1998. His teams combined to win 731 games and won six state championships and five FCIAC titles. He passed away at the age of 59 and several baseball fields and leagues throughout Stamford bear the name, "Mickey Lione, Jr." on them.
5. RAY LEGENZA (Naugatuck) The arrived at the high school in 1953 and built one of the most powerful baseball programs in the country. won four state championships and 13 league titles under Legenza. From 1970-1972, the team won a record 64 consecutive games and from 1969-1972, Naugatuck was an incredible 105-2. In his 23 years in the dugout, Legenza compiled a record of 361-80. He also coached the football team for 15 years.
4. JOE SIKORSKI (New Canaan) Known as, "The Bear", Sikorski spent 30 years (1949-79) at the high school, 20 of them as head coach of the football team. He led the Rams to seven FCIAC titles and a perfect season in 1969 as finished with a 10-0 record and state championship. As the basketball coach, Sikorski engineered the Rams to state crown in 1958 with his star player, Wilky Gilmore. He guided New Canaan to 11 state titles in Track & Field, coaching future Olympian Bill Toomey. Sikorski held the title of athletic director for 22 years before retiring in 1979.
3. JERRY MCDOUGALL (Trumbull) McDougall was a rough and tough coach straight out of central casting. He just looked he part. from 1967-1998. In football, he to 265 wins, three state championships, and five FCIAC titles. In baseball, McDougall racked up 510 victories, nine divisional titles and three FCIAC crowns. He also served at the athletic director, track & field coach and started the school's wrestling program. Died last October at the age of 76.
2. MARTY ROOS (FAIRFIELD PREP-NOTRE DAME) In January,after coaching high school hockey in the area for 40 years. He's the all-time winningest hockey coach in the state with a record of 536-301-9). Roos took over the program at in 1971 and turned into a powerhouse, winning four state championships before stepping down in 1989. He was coaxed out of retirement by two years later and subsequently led the school to a pair of state titles.
1. VITO MONTELLI () At age 79, Montelli shows no sign of slowing down. He just finished his leading the Cadets basketball team to the Class LL title. With 880 victories, Montelli is the winningest coach in the state of Connecticut. He arrived on campus in 1962 and has led St. Joe's to 11 state championships in four different divisions.
