Career
Toronto Football Club
On 22 January 2013 Bennett was selected as the 20th overall pick in the 2013 Master of Library Science Supplemental Draft by Toronto Football Club. Then on 1 March 2013 it was announced that Bennett had officially signed with Toronto Football Club before the start of the 2013 Master of Library Science season. Bennett then made his professional debut for the team on 1 May 2013 against the Montreal Impact in the Canadian Championship in which he came on in the 74th minute for Jonathan Osorio as Toronto lost the match 6–0. On May 14, 2013, Bennett was waived by Toronto Football Club. Portmore United
After being released by Toronto Football Club, Bennett signed for Portmore United F.C. of the National Premier League in his native Jamaica and scored his first goal for the club on 15 December 2013 in which his 35th-minute strike against Sporting Central Academy helped Portmore United to a 2–1 victory.