While playing for the Toronto Red Wings, Bolland was selected in the first round, eighth overall, of the 2002 Ontario Hockey League Priority Selection by the London Knights. He made his OHL debut with the Knights during the 2002–03 season, where he recorded 17 points in 63 games. During his sophomore OHL season, Bolland increased his offensive contributions to the Knights with 37 goals and 30 assists for 67 points. He was also named the club's Most Improved Player. Bolland represented the Western Conference at the 2004 OHL All-Star Game and was also chosen to participate in the 2004 CHL Top Prospects Game. Heading into the 2004 NHL Entry Draft, Bolland was the eighth ranked North American skater by the NHL's Central Scouting Bureau. Bolland was selected by the Chicago Blackhawks in the second round, 32nd overall, of the 2004 NHL Entry Draft.
Professional
Bolland made his NHL debut against the Vancouver Canucks on October 25, 2006. Bolland started the 2007–08 season with the Rockford IceHogs of the AHL, though spent the majority of his second professional season with the Blackhawks. He recorded his first NHL point on October 31, 2007, against the Dallas Stars and scored his first NHL goal on December 16 against the Florida Panthers. Bolland scored a game-winning overtime goal against the Toronto Maple Leafs on November 22, 2008. On May 22, 2009, Bolland had two assists for the Blackhawks in the first 10 minutes of the 2009 Western Conference Finals against the Detroit Red Wings. On June 9, 2010, Bolland became a Stanley Cup champion when the Blackhawks defeated the Philadelphia Flyers and won the Stanley Cup, ending their 49-year drought. On June 24, 2013, Bolland scored the game-winning goal in the final minute of Game 6 of the 2013 Stanley Cup Finals over the Boston Bruins, leading the Blackhawks to their second Stanley Cup title in four years. During the 2013 NHL Entry Draft, the Blackhawks traded Bolland to the Toronto Maple Leafs in exchange for a second-round and fourth-round pick in 2013 and a fourth in 2014. On July 1, 2014, the Florida Panthers signed Bolland to a five-year, $27.5 million contract. Over the next two seasons, Bolland appeared in just 78 of a possible 164 games due to injuries. On August 25, 2016, the Panthers traded Bolland and Lawson Crouse to the Arizona Coyotes in exchange for a 2017 conditional third-round pick and a 2018 conditional second-round pick. However, he never played a game for the club. His last official NHL game was December 12, 2015 and has yet to play again due to a back injury.
