Undrafted, Boyle played in the NHL for the Florida Panthers; Tampa Bay Lightning, with which he won the Stanley Cup in 2004; San Jose Sharks; and New York Rangers.
[1][2][3] Undrafted in any NHL Entry Draft after four years of college hockey at Miami University, the under-sized defender was signed as a free agent by the Florida Panthers on March 30, 1998.
The next season, his fourth in Florida, Boyle was traded to the Tampa Bay Lightning in exchange for a 2003 fifth-round draft pick (Martin Tůma) on January 7, 2002.
Boyle suffered a major setback, however, in September 2007, injuring himself in a freak accident after a pre-season game when a skate slipped off a hook in his locker and hit him in the left wrist, severing three tendons.
[12] Boyle was pressured to waive his no-trade clause by Tampa Bay's new ownership, who said they would otherwise place him on waivers, where he would likely be claimed by the Atlanta Thrashers.
In the opening series of the 2010 playoffs, Boyle ended game three against the Colorado Avalanche in overtime by inadvertently shooting the puck into his own net.
In the first period of the October 15, 2013, against the St. Louis Blues, Boyle was checked from behind by Maxim Lapierre into the boards, injuring his jaw and knocking him unconscious;[14] the incident led to a fight involving teammate Matt Pelech and 17 minutes worth of penalties for Andrew Desjardins.
[18] Unable to come to terms with the Islanders, Boyle opted to head to free agency, and on July 1, 2014, he signed a two-year contract with the New York Rangers.
The next year, Boyle was named as a reserve in light of injuries to Scott Niedermayer and Ed Jovanovski for Team Canada at the 2006 Winter Olympics in Turin.
[22] On February 28, 2010, the team defeated the United States to win Canada's eighth gold medal in Olympic men's hockey.
[26] During Game 1 of the 2004 Stanley Cup Finals with the Tampa Bay Lightning against the Calgary Flames, an electrical fire broke out in his Florida home, causing an estimated $300,000 worth of damage.