Kiki Chesterton took over the Wittenberg field hockey program in April 2004 after spending a year at Montclair State University in New Jersey, where she was an assistant women's lacrosse coach. She resigned after the 2004 season at Wittenberg.

While at Montclair, Chesterton earned her post baccalaureate teacher certification program in physical education. At Wittenberg, Chesterton serves as an assistant coach for women's lacrosse in addition to her field hockey responsibilities.

Chesterton was a standout lacrosse and field hockey goalkeeper at Roanoke College before graduating in 1991. She was an all-conference and all-region selection, as well as team MVP, in field hockey in 1990. She was a four-time all-conference, all-region and All-America honoree in lacrosse while helping the Maroons to three conference championships. Chesterton still owns every lacrosse goalkeeping school and conference record.

Chesterton, a native of Massachusetts who was inducted into Roanoke's Hall of Fame in 2001 and Pingree High School's Hall of Fame in 2003, began her coaching career at Kenyon College. She led the Ladies to a 9-10 record in field hockey in 1995.

She followed that by coaching at Fairleigh Dickinson University and Kean University. At Kenyon and Kean, Chesterton had a career record of 26-28 in three seasons. At Kean, the Cougars were 5-13 the season before Chesterton took over the program. In her second season at the helm, Kean went 10-9 and defeated the ninth-ranked team in the nation while playing in the challenging New Jersey Athletic Conference. As an assistant at Fairleigh Dickinson, Chesterton put together a corner unit that ranked third in NCAA Division III for corner efficiency.