Gillespie split her collegiate years at the University of Maryland and Florida State University. She served as team captain at Florida State University for the 2018-2019 and 2019-2020 seasons. In her final year, she earned WBCA Honorable Mention All-American, WBCA Region Finalist, USBWA Honorable Mention All-American, and her list of achievements continues. She earned All-ACC First Team two times and was named ACC Player of the Week three times. Gillespie is a member of the 1,000-point club.
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After graduating from Florida State, Kiah was drafted 32nd to the Chicago Sky in the 2020 WNBA Draft. She continued her playing career as she played overseas for the FIBAS Overseas in Toulouse, France.