Gilroy played in the 1998 Quebec International Pee-Wee Hockey Tournament with the New Jersey Devilsminor ice hockey team. He later played junior ice hockey in the Eastern Junior Hockey League with the Walpole Jr. Stars, Gilroy joined the college hockey ranks with Boston University of Hockey East in 2005–06. Making the team as a walk-on, he was a natural forward but was forced into the eighth defenseman position, the only available role on the team. After his third college season, Gilroy attracted attention from the NHL as an undrafted free agent, but had intentions of completing his degree at Boston University. In his senior year, in 2008–09, he was named team captain of the Terriers and recorded a college career-high 36 points in 43 games, first among Hockey East defensemen and third in the NCAA. He went on to lead the Terriers to their third Beanpot championship in four years en route to the Frozen Four Tournament. On April 10, 2009, Gilroy was announced as the winner of the 2009 Hobey Baker Award. The next day, the Terriers competed for the NCAA championship against the Miami RedHawks. Trailing 3–1 late in the third period, the Terriers rallied with two goals in the final minute to force overtime. Gilroy earned an assist on Nick Bonino's game-tying goal with 17 seconds left. The Terriers won in overtime, defeating the RedHawks 4–3, making Gilroy just the fifth player to win the Hobey Baker Award and NCAA championship in the same season. He was additionally given his third All-American honor, becoming just the third NCAA player to earn the distinction as many times, after Rick Meagher and Chris Drury.
Professional
On April 17, 2009, Gilroy signed a two-year, $3.5-million contract with the New York Rangers. He had initially been linked to both the Toronto Maple Leafs and Vancouver Canucks in contract negotiations. Gilroy signed a one-year contract as a free agent with the Tampa Bay Lightning on July 2, 2011. During the 2011–12 season, on February 27, 2012, Gilroy was traded to the Ottawa Senators in exchange for fellow defenseman Brian Lee at the NHL trade deadline. On October 7, 2012, with the 2012–13 NHL lockout in place, Gilroy was signed to an American Hockey League contract with the Connecticut Whale, marking a potential return to the New York Rangers organization. At the conclusion of the labor dispute, Gilroy was signed to a one-year contract with the Rangers on January 13, 2013. Gilroy was released to free agency by the Rangers in the off-season and, on July 8, 2013, was signed to a one-year contract with the Florida Panthers, his fourth NHL club. In the 2013–14 season, Gilroy appeared in only 16 games with the struggling Panthers before he was reassigned to the team's AHL affiliate, the San Antonio Rampage, for the remainder of the season. With limited NHL interest, Gilroy opted to forgo free agency to sign his first European contract on a one-year deal with Russian club Atlant Moscow Oblast of the Kontinental Hockey League on June 25, 2014. After one year with Atlant, and partly due to fact that Atlant would not participate in the KHL from the 2015–16 season, he signed with Spartak Moscow. As a free agent from Finnish KHL club, Jokerit following the 2017–18 season, Gilroy opted to sign a one-year deal with Swiss club, SC Rapperswil-Jona Lakers of the National League on May 15, 2018.
Personal life
Gilroy was born in North Bellmore, New York, to Frank and Peggy Ann Gilroy. Matt Gilroy is one of eight children. His father is a member of the St. John's Basketball Hall of Fame, who was drafted by the Philadelphia 76ers. He graduated in 2003 from St. Mary's High School in Manhasset, captaining the hockey team to two New York state championships. In addition to hockey, Gilroy played lacrosse at St. Mary's and was named team MVP in his junior year, in addition to all-league selections in his junior and senior years. Gilroy wears the number 97 in remembrance of his deceased brother Timmy, who died as the result of a bicycle accident at eight years old. Separated by 13 months, Matt and Timmy played on the same hockey teams growing up and wore the numbers 98 and 97, respectively, in homage to Wayne Gretzky. Traditional team policy with the Boston University Terriers does not permit players to wear high numbers deemed flamboyant and self-endorsing by Head CoachJack Parker. However, given the circumstances, Gilroy was allowed by Parker to wear 97. Gilroy also has an older brother, Frank Jr., who played basketball for St. Mary's High School and St. Anselm College. His younger brother, Kevin, joined Matt on the Terriers for their 2009 championship year. Gilroy is married to Jenny Taft, a Fox Sports 1 personality.