[2] In 2006, he spent the summer with the Palm Beach Pumas of the USL Premier Development League.
In the fall of 2007, Bennett signed with the Chicago Storm of the Major Indoor Soccer League.
Bennett played with Rochester Rhinos in the 2010 season, then re-joined Milwaukee Wave starting in the 2010-11 MISL season, then transitioned with the Wave to the MASL, where he has won multiple personal honors and a Championship with the team.
With the Milwaukee Wave taking a hiatus for the 2020–21 MASL season, Bennett joined Florida Tropics SC on a season-long loan.
The move reunited Bennett with former Wave teammates Drew Ruggles, Chad Vandegriffe, and Ricardinho Sobreira.