Jim Winstead played college tennis at UNC. Winstead won numerous city and state championships, including the North Carolina state title in 1960 and the over-50 state championship in 1981. Winstead became the tennis pro at Greensboro Country Club in 1964 and served in that capacity until 1992. Winstead was active in the growth in the Greensboro Tennis Association and a renowned teacher who coached many of the top young players in the city. Winstead was inducted into the North Carolina Tennis Hall of Fame in 1992.