On January 12, 2012, the Calgary Flames traded Holland, along with Rene Bourque and a 2nd round pick at the 2013 NHL Entry Draft (Zach Fucale), to the Montreal Canadiens in exchange for Mike Cammalleri, Karri Ramo, and a 5th round pick at the 2012 NHL Entry Draft (Ryan Culkin).

[2] In the opening month of the 2013–14 season, Holland played his first NHL game with the Canadiens against the Edmonton Oilers on October 22, 2013.

[3] On October 5, 2014, Holland and Peter Budaj were traded by the Canadiens to the Winnipeg Jets in return for Eric Tangradi.

[4] After one season within the Jets organization, Holland signed a one-year contract in Finland with Liiga club, HPK, on June 16, 2015.

Opting to end his professional career, Holland enrolled in the University of Victoria in pursuing a degree in Computer Science.