As a player, McEnroe played as a linebacker and an offensive lineman at Taft Union High School in Taft, California from 1984 to 1987. During high school, he earned First Team All-SSL Offense and Defense and was picked to the Bakersfield Californian All-Area team. During his high school career, he was also voted the Most Valuable Lineman and Team Captain. In 1989, he played for Bakersfield College before playing for the Cal Lutheran Kingsmen during the 1991 and 1992 seasons. At Cal Lutheran, he received First Team All-SCIAC at Center and also Most Inspirational Player honors as team captain for the football team in his senior year.[3][4] In his senior year, 1992, he was also named to the All-SCIAC first team.[5][6]
McEnroe was the offensive line coach at Humboldt State University in 1999 to 2002 and was hired as head football coach at West Hills Chaminade in 2003.[8] He had been a coach at West Hills Chaminade High School the last four years when he was hired at California Lutheran in 2007.[9] After over ten years of coaching, he became the fourth head football coach in the history of Cal Lutheran. In his four years as coach of the Chaminade Eagles, the team compiled a 32–16 record with four consecutive CIF playoff appearances and a top 10 ranking each year. The team won the Mission League Championship and advanced to the CIF semifinals.[10]
McEnroe's wife, Kami, is a coach for the California Lutheran's cheerleading squad. They met at Bakersfield College, where Ben played and Kami was a cheerleader.[13] McEnroe has been married to Kami since 1985, and they have three children, Kassidy, Cory and Kylie.[3] He earned a bachelor's degree in history (1993) and a Master of Arts degree in education (1999) from Cal Lutheran.[3]