Bob Sheffler was a Middletown High School All-County player, 1972 Boston University team captain, and Mason Dixon League standout 1973–1977. During a 20-year coaching career at Middletown High School, he produced state, regional, county, and MVAL championship teams. Altogether, Sheffler compiled a 224–39–7 record. In 1992, he was nominated by the National Federation as one of this nation’s most outstanding coaches. Sheffler was also named the Mathematics Teacher of the Year in 1988. He has gained the respect of his peers as a gifted coach and innovative educator, and is the “winningest” soccer coach in the county history.