Dr. Gillespie received a Bachelor of Science degree in chemistry and Molecular Biology from Vanderbilt University in Nashville, Tennessee in 1981, and received his Doctor of Medicine from Vanderbilt University in 1981. In 1982, he completed his flexible internship at Evanston Hospital (Affiliate of Northwestern School of Medicine) in Evanston, Illinois. Dr. Gillespie completed his Ophthalmology residency at the University of Virginia Hospital in Charlottesville, Virginia in 1985.

Dr. Gillespie is trained in LASIK, refractive surgery to correct nearsightedness, farsightedness, and astigmatism and is certified with the VISX Excimer Laser. He has over 9 years experience in refractive surgery including radial keratotomy, photorefractive keratotomy and LASIK. He is the Fellow of the American Academy of Ophthalmology, and a member of the Kentucky Medical Association, American Medical Association, Outpatient Ophthalmic Surgery Society and American Society of Cataract & Refractive Surgery. Dr. Gillespie has been in adult and pediatric general ophthalmology practice in Paducah, Kentucky since 1985. He has performed several thousand cataract surgeries with intraocular implants. He currently serves as Medical Director for the Eye Surgery Center of Paducah.  Dr. Gillespie was chosen as a recipient of the 2004 Top LaserVision Surgeon Award.

Dr. Gillespie is a volunteer physician for the St. Nicholas Family Clinic, volunteering his physician services and time.

Dr. Gillespie is the parent of a son, Will and a daughter, Abigail. He enjoys playing golf and tennis in his spare time.