Career
Before playing in the NHL, Sheary played four years with the UMass Minutemen of Hockey East.
He was not drafted by an NHL team. On July 1, 2015, Sheary signed a three-year entry-level contract to join the Pittsburgh Penguins of the National Hockey League (NHL). He was sent down to play for their AHL-affiliate Wilkes-Barre/Scranton Penguins.
On December 16, 2015, Pittsburgh called him up and Sheary made his NHL debut in a 3–0 loss against the Boston Bruins. Two days later on December 18, Sheary scored his first NHL goal against Tuukka Rask in a 6–2 loss against the Boston Bruins. He also recorded an assist on a Trevor Daley goal.
He helped the Penguins during the playoffs. They defeated the New York Rangers, Washington Capitals, and Tampa Bay Lightning. They eventually went on to defeat the San Jose Sharks four games to two in the Finals to win the Stanley Cup. On January 23, 2017, the league named him as the First Star of the Week. That season, he helped the team reach their second-straight Finals, as the Penguins went on to defeat the Nashville Predators four games to two to win repeat as Stanley Cup champions. On July 30, 2017, Sheary signed a three-year, $9 million contract to stay with the Penguins.
On June 27, 2018, the Penguins traded Sheary along with Matt Hunwick to the Buffalo Sabres in exchange for a 2019 conditional fourth-round draft pick. He played two seasons with the Sabres.
On February 24, 2020, the Sabres traded Sheary along with Evan Rodrigues back to the Pittsburgh Penguins in exchange for the Dominik Kahun. He scored 1 goal and recorded 3 assists in 8 regular season games, as well as, recording 2 assists in four playoff games in his return with the Penguins.
On December 22, 2020, Sheary signed a one-year, $735,000 contract to join the Washington Capitals. On April 14, 2021, Sheary signed a two-year, $3 million to stay with the Capitals.
On July 1, 2023, Sheary signed a three-year, $6 million contract to join the Tampa Bay Lightning. He played two seasons with the Lightning. On June 29, 2025, the Lightning placed Sheary onto waivers and terminated his contract.
On October 6, 2025, Sheary signed a one-year contract to join the New York Rangers. He scored seven goals and eleven assists in 62 regular season games with the Rangers.
On July 1, 2026, Sheary signed a one-year, $850,000 contract to rejoin the Buffalo Sabres.
