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.
Yakupov is considered the best pure goal-scorer from the 2012 NHL Draft. In addition to great hands, Yakupov may be the best skater in the draft. The main negative for Yakupov is that he's more of a pure finisher than an overall offensive talent; he needs to work on involving his teammates more and setting up plays. The smallish Yakupov also experienced some injury problems in 2011-12, something that could be a problem in an NHL increasingly ruled by big men.
Yakupov played in the KHL during the NHL lockout, but is now playing for the Edmonton Oilers. The offensively talented winger should see playing time on the team's second line but could be moved down to the third line if he struggles to adjust to the NHL level or to reduce the pressure for him to score goals.