2009-10: Nail Yakupov played for Reaktor Nizhnekamsk in Russia's MHL. In 14 games, he scored 4 goals and added 2 assists for 6 points. Yakupov was chosen in the first round, 19th overall, of the 2010 KHL Draft by Neftekhimik Nizhnekamsk. Yakupov also was chosen in the first round, 2nd overall, of the 2010 CHL Import Draft by the OHL's Sarnia Sting.
2010-11: Yakupov moved to North America to play for the Sarnia Sting. In his OHL rookie season, Yakupov played in 69 games for the Sting, scoring 49 goals and adding 52 assists for 101 points on the season. For his efforts, Yakupov was named both the OHL Rookie of the Year and CHL Rookie of the Year. He was named to the OHL's First All-Rookie Team. Yakupov played for Russia at the 2011 U-18 World Junior Championship, scoring 6 goals and adding 7 assists for 13 points in 7 games for the bronze medal squad.
2011-12: Yakupov was limited to 42 regular season games in his second OHL season due to nagging injuries and his participation in the 2012 U20 World Junior Championship. Despite his shortened season, he finished as the Sting's second-leading scorer with 31 goals and 38 assists and was rated the top North American prospect by Central Scouting heading into the 2012 NHL Draft. Yakupov returned for the Sting's six-game first round playoff series against Saginaw and scored 2 goals with 3 assists and was minus-7 with penalty minutes for the series. Skating for Russia at the WJC, he had a team-high nine assists and was plus-5 in seven games. Russia advanced to the gold medal game – falling to Sweden, 1-0.
2012-13: Yakupov played in all 48 games for the Oilers and led all NHL rookies with 17 goals; finishing tied for most points (31) with Calder Trophy winner Jonathan Huberdeau. Skating on Edmonton's second line, he had 14 assists and was -4 with 24 penalty minutes, scoring 6 of his 17 goals on the power play. Yakupov skated for Nizhnekamsk in the KHL during the NHL lockout and was the captain for Russia's junior team in the 2013 World Junior Championship. He score 9 goals with 9 assists and was -4 with 33 penalty minutes in 22 KHL games. In seven games for Russia he scored 3 goals with 5 assists and was +2. Russia captured a bronze medal on home ice in Ufa, defeating Canada 6-5 in overtime in the bronze medal game.
Yakupov is a pure goal-scorer with great hands, quick feet, and great natural hockey sense. Prior to his NHL debut here was concern about Yakupov’s ability as a playmaker and being more of a pure finisher than someone who involves his linemates, but he proved to be a solid team player who adjusted well to the NHL atmosphere. Although not overly big at 5'11 and sometimes prone to injury, Yakupov showed no signs of struggle in his big league debut.
Yakupov will play his second season with the Edmonton Oilers. The offensively talented winger should see increased playing time likely on the team's second line, continuing to contribute to the Oilers’ goal-scoring efforts.