He then joined the college ranks with the Minnesota-Duluth Bulldogs of the Western Collegiate Hockey Association (WCHA) for a two-year tenure there, as well.

After spending parts of two seasons with their American Hockey League (AHL) affiliate, the Manitoba Moose, he joined the club full-time in 2007–08.

[2] Raymond had been hesitant about pursuing his career due to a lack of interest from major junior teams, but his friend Dan Bertram encouraged him to play with him in Camrose.

[1] He consulted with Kodiaks head coach Boris Rybalka and was challenged to improve at the Junior A level before moving to Minnesota-Duluth.

[1] As a result, Raymond remained in Camrose, signing a letter of intent in November 2004 to join the Minnesota-Duluth the following year for the 2005–06 season.

Though he missed the final against the British Columbia Hockey League's Surrey Eagles, the Kodiaks won without him and advanced to the 2005 Royal Bank Cup, Canada's national Junior A tournament.

[3][9] He was scouted by Canucks general manager Dave Nonis as a fast skater with the puck who needed to work on his strength.

[11] Raymond chose to forgo his final two years of college eligibility to turn professional and signed an amateur tryout contract with the Canucks' minor league affiliate, the Manitoba Moose of the AHL.

[15] Succeeding at the AHL level, Raymond recorded a five-point game with a hat trick and two assists during a match against the Rochester Americans on November 21, 2007.

[18] Known for his skating ability, Raymond won the fastest skater segment of the Canucks' 2008 SuperSkills Competition with a time of 14.283 seconds.

[25] Raymond enjoyed a breakout campaign in his third NHL season, playing regularly on the Canucks' second line with centre Ryan Kesler and newly acquired winger Mikael Samuelsson.

Prior to the final game of the season on April 10, 2010 against the Calgary Flames, he was voted by the Canucks' booster club to receive the Fred J. Hume Award as the team's "unsung hero".

[28] Becoming a restricted free agent on July 1, 2010, Raymond filed for salary arbitration after initially failing to come to terms with the Canucks.

On a team basis, the Canucks won their first-ever Presidents' Trophy, having accomplished the best regular-season record in the NHL that year.

Entering the 2011 playoffs as the first seed in the West, they eliminated the defending Stanley Cup champion and eighth-seeded Chicago Blackhawks along with the fifth-seeded Nashville Predators and the second-seeded San Jose Sharks in the first three rounds to advance to the Stanley Cup Finals for the first time in 17 years matching up against the third-seeded Boston Bruins.

"[35] No penalty was called on the play nor did Boychuk receive any discipline from the league following the game, which drew public criticism from Canucks general manager Mike Gillis.

Unable to train on the ice or with weights, Raymond spent the 2011 off-season largely inactive, with the exception of cardiovascular workouts in preparation for the upcoming 2011–12 season.

[35] Five-and-a-half months after sustaining his back injury, Raymond was set to return to the Canucks' lineup for a game against the Nashville Predators on December 1, 2011.

[37] However, the team failed to file the proper paperwork to the NHL by the 5 p.m. deadline, delaying Raymond's return until the following game on December 4 against the Calgary Flames.

Despite their continued regular season dominance, the Canucks would fall in five games in the first round of the 2012 playoffs by the eighth-seeded and eventual Stanley Cup champion Los Angeles Kings.

Raymond would play 46 games and recording 10 goals, 12 assists and 22 points in the lockout-shortened 2012–13 season for the Canucks as they finished the season as the third seed in the West before getting swept in the opening round of the 2013 playoffs by the sixth-seeded San Jose Sharks with Raymond recording a goal and an assist for two points in all four games.

Despite not being a physical player, Raymond gained notoriety in Toronto when he threw a hard hit on Senators' defenceman Chris Neil in the first period.

[45] On July 4, 2016, Raymond signed a one-year contract as a free agent with the Anaheim Ducks, reuniting with former Canuck teammates Ryan Kesler and Kevin Bieksa.

[46] After making the Ducks opening night roster for the 2016–17 season, Raymond appeared in four scoreless games in a depth role before he was reassigned to AHL affiliate, the San Diego Gulls.

[47] In an interview with SportsNet on January 3, 2017, Raymond revealed that he refused to report to the AHL largely to spend time with his wife, who had been diagnosed with Lyme disease.

[49] Following his 2010 playoff run with the Canucks, Raymond was added to Team Canada's roster for the 2010 IIHF World Championship in Germany, his first international tournament.