Amateur Two years into his three-year
major junior career with the
Western Hockey League (WHL)'s
Medicine Hat Tigers, Lupul was drafted by the
Mighty Ducks of Anaheim as the team's first choice, seventh overall, at the
2002 NHL entry draft. The
London Knights'
Rick Nash was chosen first and Lupul's Tigers teammate
Jay Bouwmeester went third that year. The following season, Lupul made the final
roster for
Canada and played in the
2003 World Junior Ice Hockey Championships in
Halifax,
Nova Scotia. during his time with Anaheim.
Mighty Ducks of Anaheim and Edmonton Oilers Lupul made the jump directly to the Anaheim lineup his first season out of the WHL, but the following season, during the
2004–05 NHL lockout, he was assigned to the team's
American Hockey League (AHL) affiliate, the
Cincinnati Mighty Ducks, for the entire
season. However, in his third professional season, Lupul was a regular with Anaheim and during the team's run in the
2006 Stanley Cup playoffs, he became the first player in NHL playoff history to cap a three-goal game with an overtime goal after he tallying all Duck goals in a 4–3 win over the
Colorado Avalanche in Game 3 of the
Western Conference Semifinals. After the
2005–06 season, Lupul was traded to the Western Conference champion
Edmonton Oilers (along with
Ladislav Šmíd and draft picks) in exchange for
Chris Pronger on July 4, 2006.
Philadelphia Flyers On July 1, 2007, after just one season with Edmonton in which he scored 16 goals, Lupul was traded (alongside Oilers captain
Jason Smith) to the
Philadelphia Flyers in exchange for
Joni Pitkänen,
Geoff Sanderson and a third-round draft pick in
2009. During the
2007–08 season, his first with the Flyers, Lupul was diagnosed with a spinal cord contusion after a collision with teammate
Derian Hatcher in a game against the
Toronto Maple Leafs on January 5, 2008. Lupul made his return to the lineup just over one month later, on February 9 in a game against the
New York Rangers. On April 22, Lupul scored the series-winning goal in the first overtime of Game 7 in the
Eastern Conference Quarterfinals between Philadelphia and the
Washington Capitals. After helping the Flyers reach the Eastern Conference Finals, in which Philadelphia fell to
rivals Pittsburgh, Lupul agreed to a four-year contract extension with the team on July 21.
Return to Anaheim On June 26, 2009, following his second season with Philadelphia and just one year into his four-year contract, Lupul was traded by the Flyers to the Anaheim Ducks at the
2009 NHL entry draft (along with
Luca Sbisa and two first-round picks) in exchange for Chris Pronger, the second time in Lupul's career he had been part of a trade involving the Ducks with Pronger going the other way. Back surgery in December 2009 and a subsequent blood infection limited him to just 23 games during the season. He ultimately missed a total of 12 months of playing time—the final 59 games of that season and carrying over into the first 28 games of the following
2010–11 season.
Toronto Maple Leafs On February 9, 2011, nearing the end of his second season back with Anaheim, but having played only 49 games during his second stint, Lupul was traded (alongside
Jake Gardiner and a conditional draft pick in
2013) to the Toronto Maple Leafs in exchange for
François Beauchemin, marking the third time Lupul had been involved in a trade with the Ducks organization. Originally, the deal excluded Lupul, however he was included as a salary dump to keep the Ducks under the
salary cap. After being traded to Toronto, he made the transition from right to left wing and finished with 18 points in 28 games to finish the
2010–11 season. The following year,
2011–12, Lupul began the year on the opposite wing of
Phil Kessel, putting together a strong first half of the season that led to his invitation to the
2012 NHL All-Star Game in
Ottawa as an alternate captain to
Zdeno Chára. There, he scored two goals for Team Chara in a 12–9 win over Team
Alfredsson. On March 2, 2012, Toronto fired its head coach,
Ron Wilson, and replaced him with
Randy Carlyle, Lupul's former head coach in Anaheim. Lupul suffered a severe shoulder separation on March 6 that necessitated immediate season-ending surgery. Nonetheless, he finished with a career-high of 67 points on the year despite playing in just 66 games, marking the first time in his NHL career he scored at least a point-per-game pace. At the end of the season, Lupul was a finalist for the
Bill Masterton Memorial Trophy—awarded annually to the NHL player best exemplifying qualities in perseverance, sportsmanship and dedication to hockey—which was ultimately awarded to
Max Pacioretty of the
Montreal Canadiens. During the
2012–13 NHL lockout, Lupul played for the
Kontinental Hockey League (KHL)'s
Avtomobilist Yekaterinburg in
Yekaterinburg,
Russia. After the lockout was resolved and just prior to the start of the
truncated 2012–13 season, Lupul, along with teammate
Clarke MacArthur, was named an alternate captain of the Maple Leafs under captain
Dion Phaneuf. Days later, on January 20, 2013, Lupul signed a five-year, US$26.25 million contract extension with Toronto. Only three games into the season, Lupul fractured his right forearm when he was hit by a Phaneuf slapshot while screening opposing goaltender
Marc-André Fleury in a game against Pittsburgh. Lupul subsequently missed 25 games. In his return to the ice on March 16, he scored on his first shift of the night and once again in the second period of the game. However, the Maple Leafs went on to lose the game in a ten-round
shootout to the
Winnipeg Jets. Rejuvenated in his return after a long absence, Lupul scored goals in six consecutive games and recorded points in a prolific rate—eight goals and six assists in six games—before he suffered another injury in a game against his former club, the Flyers. While chasing the puck deep in his own zone, Lupul was hit by two Flyers simultaneously, one of which accidentally contacted his head, resulting in a
concussion. He would miss an additional two weeks before making his return on April 16 against Washington. Lupul finished the season with totals of 18 points in 16 games. With 57 points gained in 48 games, the Maple Leafs qualified for the playoffs for the first time since
2004. During Game 2 of the
Eastern Conference Quarterfinals against the
Boston Bruins, Lupul scored two goals to help propel the Leafs to a 4–2 win and even the series at one game apiece. He would score again in Game 4 at the
Air Canada Centre when he scored the game's opener, though Toronto would eventually lose in overtime, 4–3. Lupul ended his first playoff series with Toronto with three goals and one assist in seven games as the team fell 5–4 in overtime of Game 7. On November 14, 2015, Lupul scored his 200th career goal during a 4–2 victory over the
Vancouver Canucks. On December 1, 2015, Lupul was placed on injured reserve after suffering a lower body injury. Lupul returned but was again injured in February, and was shut down for the season to have surgery. At the end of the season, Lupul was not seen at the year-end locker room clean-out or media briefings. Despite comments from Lupul earlier in the season and teammate
Nazem Kadri in the summer implying Lupul wanted to and had the ability to play the following season, he did not participate in pre-season action, and he announced on September 22, 2016, he would sit out the upcoming season due to injury. He was subsequently placed on the long-term injury reserve, with the team stating he had failed his pre-season physical. Lupul was left unprotected by the Maple Leafs in the
2017 expansion draft and was thus eligible to be selected by the expansion
Vegas Golden Knights, although players who were injured for more than one year and were not expected to play again were exempt in the draft under NHL rules, signalling that Lupul may not be injured in the traditional sense. In September 2017, the Leafs declared Lupul had failed his physicals at training camp before the
2017–18 season. Lupul then made several posts on his
Instagram account saying he was healthy and accused the Maple Leafs of cheating by designating him injured so his salary could not count against the
salary cap. These accusations prompted the NHL to administer a second physical by an independent doctor, which he subsequently failed and confirmed the Maple Leafs' initial claim he was unfit to play. ==International play==