Gillespy began running her freshman year of high school. Her 5K PR is 18:56. She also played varsity basketball all four years. She suffered a pelvic stress fracture at the end of basketball season that limited her track season. Gillespy placed 24th and 17th at her State Cross Country Championships.
Gillespy was awarded: The Sr. Rose Ellen Award: Outstanding Female Athlete, The Rotary Club Athletic/Academic scholarship, The United States Marine Corps Distinguished Athlete Award, The Bright House Breakfast of Champions Award for Cross Country (twice) and the Orlando Sentinel Cross Country Athlete of the Year (twice).
Gillespy ranked fifth in her class with a total GPA of a 4.371. She was Ambassador President, SGA Vice President, Cross Country/Track Captain and Basketball Captain. She was very active in the math Alpha-Theta Club, National Honor Society and National Honor Society for Spanish.