Engelland played for the Pittsburgh Penguins, Calgary Flames and Vegas Golden Knights over his eleven-season career in the National Hockey League (NHL).

He turned professional in 2003–04 and split that season between the Las Vegas Wranglers of the ECHL and the Lowell Lock Monsters of the American Hockey League (AHL).

[3] Returning to Las Vegas, Engelland played the entire 2004–05 season in the ECHL where he scored 5 goals, added 16 assists and recorded 138 penalty minutes.

[1] When a labour dispute delayed the start of the 2012–13 NHL season, Engelland opted to sign with Rosenborg IHK in Norway's GET-ligaen.

[1] In his fourth NHL season, 2013–14, Engelland posted a career high of six goals (and added six assists) in a campaign where the Penguins occasionally played him at forward.

Engelland opted to leave the Penguins following the season and signed a three-year, $8.7 million contract with the Calgary Flames, where he hoped to earn expanded responsibilities with the rebuilding team.

[12] However at the start of 2017 Engelland was made alternate captain of the Flames during the absence of Troy Brouwer, who was on injured reserve with a broken finger.

Engelland immediately signed a one-year, $1 million deal with the Golden Knights, marking his return to professional hockey in the city.

[15] On April 23, 2018, Engelland was nominated by the Knights for the King Clancy Memorial Trophy as a player who best exemplifies leadership qualities and gives back to his community.

[11] His father is a welder by trade, and the family moved frequently in his early life as he lived in the Edmonton-area communities of Leduc and Mayerthorpe before settling in Chetwynd, British Columbia.