Bolland also skated in the American Hockey League (AHL) for the Norfolk Admirals and Rockford IceHogs.

Bolland was born June 5, 1986, in Etobicoke, now a part of Toronto, Ontario, and lived in the Mimico neighbourhood.

[2] Bolland was a member of the Bantam All-Ontario champions Toronto Red Wings with future Chicago Blackhawk teammate Bryan Bickell.

[1] During his sophomore OHL season, Bolland increased his offensive contributions to the Knights with 37 goals and 30 assists for 67 points.

On May 22, 2009, Bolland had two assists for the Blackhawks in the first 10 minutes of the third game of the third round series against the defending Stanley Cup champion Detroit Red Wings.

[7] The Blackhawks would eventually get defeated by the second-seeded and defending Stanley Cup champion Red Wings in five games.

On November 10, Bolland underwent surgery to repair a herniated disk in his back, taking him out of the Blackhawks line-up for the next 41 games.

On October 29, 2010, Bolland suffered a rib injury in a 7–4 loss to the Edmonton Oilers, resulting in him missing the next four games.

The defending Stanley Cup champion and eighth-seeded Blackhawks would become the seventh team in league history to force a game seven after initially having a 3–0 series deficit.

Bolland would record seven goals and assists for 14 points in 35 games in the lockout-shortened 2012–13 season as the Blackhawks won the Presidents' Trophy.

On June 30, 2013, 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.

Bolland's last official NHL game was December 12, 2015 (while he was still with the Panthers), and in October 2016 his agent acknowledged that he would likely never play again due to a back injury.