Sherrill Kester Dempsey was inducted into the Westchester Athletic Hall of Fame in 2009. She scored 115 goals on the soccer field for the Wildcats. She was named soccer MVP in 1992, 1993, 1994, 1995, and 1996, and earned Academic All-Conference honors in 1995 and 1996. She was All-Region in 1994, 1995 and 1996, and was Player of the Year in 1995. She was named to the National All-South Region in 1996, and All-State in 1995 and 1996. She was a soccer state champion in 1995 and 1996. A two-sport athlete, Dempsey also was a basketball Conference Player of the Year in 1994, 1995, and 1996, and basketball MVP in 1994, 1995, and 1996. She was named All-State in 1994, 1995, and 1996, and was a basketball State Champion in 1993. She won the Female Athlete of the Year Award in 1994, 1995, and 1996, and the Female Scholar Athlete of the Year Award in 1995.

Dempsey earned a soccer scholarship to Duke University, where she was All-ACC in 1996, 1998, and 1999; a member of All-American Freshman Team in 1996, the All-American Third Team in 1999, and the All-Southeast Region Team in 1996, 1998, and 1999. She was named to the ACC 50 th Anniversary Team, which included only the top 50 female ACC soccer players, and was Academic All-ACC in 1999 and 2000. Dempsey was the 14th overall pick in 2000 WUSA draft and played for the San Diego Spirit. She was the Spirit’s Player of the Year in 2002. She also played for the U.S. National Team in 2000, which competed in the Australian Cup.