Before USL: Bennett signed his first professional contract in August 2016 with Cypriot side Anorthosis Famagusta FC. He spent six months with the team but did not make an appearance. Bennett has previously trained with FC Cologne in Germany and AIK Stockholm in Sweden.
College: Bennett attended Marquette University and tallied nine goals and 14 assists in 55 games for the Golden Eagles. He was named the team's Freshman of the Year for the 2013 season and also earned College Soccer News All-Freshman Second Team and Big East Men's Soccer Championship All-Tournament Team honors. Bennett was Unanimously selected to the Big East All-Rookie Team. During his sophomore year, Bennett was named to the All-Big East First Team after leading Marquette with six assists, while he also earned a Big East Offensive Player of the Week accolade late in the season. As a junior, Bennett II earned Second Team All-Big East honors.