Bennett began his playing career for the Kings School, and went on to earn selection to the heralded Australian Schoolboys representative side. In 2009, Bennett was selected for Super Rugby’s NSW Waratahs’ Junior Squad. He played for the team for two years, simultaneously making appearances for the Eastern Suburbs Rugby Club. He stayed with Eastern Suburbs until 2014, and was selected for the Australian Barbarians RC touring side at the end of that season.
In 2015, Bennett moved to the United States, and lit up the Pacific Rugby Premiership from the moment he arrived. He was a staple for Santa Monica RC, and won PRP Rookie of the Year honors. This led to a professional contract with the now defunct Sacramento Express, where he was a regular starter.
In 2016, Bennett moved coasts, and led the New York Athletic Club to a national championship appearance, alongside RUNY signings Chris Mattina, Nate Brakeley, and others. He was signed to play for RUNY during the 2018 exhibition season, and made 1 appearance against the Toronto Arrows, before succumbing to injury.