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Dr. Caldwell grew up in Edmonton and obtained his dental degree from the University of Alberta in 1990. He then practiced general dentistry for 7 years in northeast Edmonton. Dr. Caldwell moved to Toronto to continue his dental education in 1997 at the University of Toronto. He obtained a Master of Science degree and completed the Pediatric Dentistry Specialty Program.
In 2000, he returned to Edmonton to deliver dental services to pediatric patients in the city.