While only a rookie, Bennett was placed on the top forward line alongside team captain Denver Manderson at center and Alex Szczechura at left wing.

[citation needed] Bennett had a strong start to his season before being named to represent the United States at the 2009 World Junior A Challenge.

In December 2009, he was named top forward at the Canadian Junior Hockey League (CJHL) prospects games in Winkler, Manitoba.

After receiving a pass, he beat the Vipers' defenders and approached the right side of the net, followed-up by teammate Denver Manderson as well as Vernon defensemen.

Feinting an attempt at a wraparound goal, he used a backhand pass through his skates to Manderson that the Vernon goaltender, Graeme Gordon, did not notice.

[15] Bennett's play during the regular season earned him a spot in the starting lineup for the Penguins' first game in the 2013 Stanley Cup playoffs.

He scored a power play goal in his first-ever playoff game, coming against New York Islanders goaltender Evgeni Nabokov on May 1.

[17][18] He had surgery the following week and returned to the lineup four months later on March 28, 2014, in a game against the Columbus Blue Jackets, where he scored the game-winning goal in a 2–1 Penguins victory.

[23] As a free agent after his lone season with the Devils, Bennett signed a one-year, $650,000 contract with the St. Louis Blues on July 1, 2017.

[24] In the following 2017–18 season, after attending the Blues' training camp, Bennett was placed on waivers and reassigned to begin the year with the club's AHL affiliate, the Chicago Wolves.

[citation needed] In the off-season, as a restricted free agent, Bennett opted to halt his North American career after agreeing to a one-year contract with Belarusian club Dinamo Minsk of the Kontinental Hockey League (KHL) on July 6, 2018.

[25] In the 2018–19 season, Bennett appeared in five games with Minsk, registering one assist before opting to mutually terminate his contract with the club on September 19, 2018.