Caldwell had teamed up with noted West Coast coach Randy Bennett in Victoria during 2009, he also coached Canadian Olympic medallist Ryan Cochrane. This move was credited for her successful upturn and focus on the backstroke while being previously looked at as a competitor in the individual medley.[6]
She continued to perform well under the tutelage of Bennett, Caldwell next swam to a bronze medal at the 2014 Commonwealth Games in her feature event, the 200 m backstroke.[7] She also swam in the 50 and 100 m backstroke.[4] The next year, she followed that up with a gold medal at the 2015 Pan American Games in Toronto.[7] The win was an emotional one has it came just months after the death of her esteemed coach, Bennett, who helped propel her to such heights.
For the 2016 Summer Olympics, Caldwell was named to Canada's Olympic team.[8] In the 200 m metre backstroke event, Caldwell swam to a bronze medal. After the event she told CBC reporters that the previous year was hard and she wanted to make her new coach Ryan Mallette proud.[9]
^"Hilary Caldwell". London 2012. The London Organising Committee of the Olympic Games and Paralympic Games Limited. Archived from the original on July 30, 2012. Retrieved September 13, 2012.