Bennett founded the ib26 Futbol Academy, which focuses on developing soccer techniques and tactics. He currently plays professionally for the Milwaukee Wave of the Major Arena Soccer League, where he has won two championships, earned two league MVP awards, and scored over 450 goals during his 14-year tenure with the Wave. He has also racked up 492 goals over 307 appearances for the club.

Bennett has also played for numerous professional and semi-professional organizations, including the Milwaukee Torrent, the Charleston Battery of the USL 1, and internationally for his home country of Canada on the beach and futsal squads.