Prior to enrolling at the University of New Hampshire, Bobby played three seasons with the Boston Jr. Bruins of the Eastern Junior Hockey League from 2003–2006, and five seasons with Marlborough High School from 2000–2005, making the varsity team as an eighth-grader. During the 2004–05 season, he helped both his high school team and junior team to championship titles. At MHS, he recorded 284 points in 116 games as well as breaking the school’s record in goals scored during his junior year, tallying 58 goals in 25 games.

Bobby was named the UNH Wildcats’ co-captain and finished second among all NCAA Division I players in goals in 2009 – 10, scoring 29 for UNH, earning him a nomination as a finalist for the Hobey Baker Award as the top U.S. college hockey player. On March 24, 2010, he was recognized as the 58th recipient of the Walter Brown Award, which is presented annually to the best American-born college hockey player in New England. Bobby was also selected as Hockey East’s Player of the Year, an All-Hockey East First Team honoree, the Hockey East Player of the month for November, the Hockey East scoring champion, a Hockey East Three Stars Award winner and a 2010 Hockey Humanitarian nominee for his efforts in the community.

Bobby is currently playing for Hartford Wolfpack. He also played formally for the Milwaukee Admirals of the American Hockey League, Florida Panthers, Ottawa Senators, New Jersey Devils and Nashville Predators, and won the 2011 Calder Cup championship (American Hockey League) while with the Binghamton Senators. Bobby was also picked to represent the United States of America for Men’s Hockey team at the 2018 Winter Olympics in South Korea.