Coach Justin Cunningham is entering his seventh season as the head football coach at Leonardtown High School, where he has led the Raiders to unprecedented success, including the program’s first ever regional championship. A Calvert High School and University of Maryland graduate, Coach Cunningham brings a deep-rooted passion for developing athletes and building high character teams.
Before taking over at Leonardtown, he served as an assistant strength coach at the University of Maryland, and as an assistant coach at both Calvert High School and the nationally renowned DeMatha Catholic High School. At DeMatha, he held multiple roles including head freshman football coach, linebackers coach, wide receivers coach, tight ends coach, offensive line coach, strength and conditioning coach, and associate head coach. His versatility and leadership helped shape one of the most competitive high school football programs in the country.
Throughout his coaching career, Coach Cunningham has helped guide over 100 student athletes to play college football and has contributed to the development of more than 10 players who advanced to the NFL. Known for his emphasis on discipline, toughness, and player development, he remains dedicated to mentoring young men and young women both on and off the field.
