Career
Undrafted, Sheary played collegiate hockey with the University of Massachusetts of the Hockey East. At the conclusion of his senior season with the Minutemen, Sheary made his professional debut with the Wilkes-Barre/Scranton Penguins of the AHL at the tail end of the 2013-2014 season, and remained with the club into the post-season to produce 11 points in 15 games. On July 1, 2015, Sheary was signed to a two-year entry-level contract with the National Hockey League affiliate of Wilkes-Barre, the Pittsburgh Penguins.
In the following 2015-2016 season, Sheary was recalled from the AHL to the Pittsburgh Penguins on December 15, 2015 and made his National Hockey League debut on December 16, 2015 in a 3–0 loss against the Boston Bruins.
On December 18, 2015, he scored his first National Hockey League goal on goaltender Tuukka Rask of the Boston Bruins and registered his first National Hockey League assist in the same game. On March 13, 2016. Sheary recorded his first multi-goal game.
Scoring 2 goals against the New York Rangers at Madison Square Garden against goaltender Henrik Lundqvist.
