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As a free agent, Yakupov opted to leave the NHL and return to Russia to further develop his game. He agreed to a two-year contract with perennial contending club, SKA Saint Petersburg of the KHL on July 3, 2018.

Yakupov was set to be a restricted free agent, but with a $2.5 million qualifying offer the Blues declined to renew, he became an unrestricted free agent. Despite gaining KHL interest, Yakupov was determined to continue in the NHL, and on July 4, 2017, he signed a one-year, $875,000 contract with the Colorado Avalanche.

On October 7, 2016, Yakupov's tenure with the Oilers ended in the lead up to the 2016–17 season, as he was traded to the St. Louis Blues in exchange for prospect Zach Pochiro and a conditional third-round pick in 2017. After attending training camp and pre-season, he made the Blues opening night roster, making his debut in a 5–2 victory over the Chicago Blackhawks on October 12, 2016. In his next game the following day, he scored his first goal with the Blues and added an assist in a 3–2 victory over the Minnesota Wild. After initially providing an offensive spark with 4 points in his first 6 games, Yakupov's contributions dried up and he was made a healthy scratch by the Blues 12th game under head coach Ken Hitchcock. Appearing in a depth role with the Blues, Yakupov was exposed to limited ice time. After Hitchcock's departure, Yakupov appeared in just 11 further games out of 27 after he was made a frequent healthy scratch by Mike Yeo. His season was ended prematurely after suffering a knee injury, which required surgery, against the Colorado Avalanche on March 31, 2017. He completed his season with 3 goals and 6 assists for 9 points in 40 games, all career lows.

The lockout ended in January 2013 and Yakupov returned to North America to play for the Oilers. A fan of Pavel Bure growing up, Yakupov wanted to have the number 10 on his jersey, the same one Bure wore for most of his career. However, since Shawn Horcoff wore that number at the time, Yakupov instead chose to wear number 64, as the two digits added up to 10. Yakupov played his first NHL game in the first Oilers game on 20 January 2013, against the Vancouver Canucks. He scored his first goal during the next game, the Oilers' home opener, against Antti Niemi of the San Jose Sharks on 22 January.

On 27 April 2013, Yakupov recorded his first career hat trick in a 7–2 victory over the Vancouver Canucks, with all three goals coming in the third period. Yakupov finished his rookie season leading all rookies in goals with 17, and tied with Jonathan Huberdeau for points with 31. Yakupov also scored 11 goals in the month of April, second only to fellow countryman Alexander Ovechkin.

During the 2012 NHL Entry Draft on 23 June 2012, Yakupov was picked first overall by the Edmonton Oilers. On 23 July, the Oilers signed Yakupov to a three-year entry level contract.

As a result of the 2012–13 NHL lockout, the Oilers had assigned Yakupov to Sarnia for the 2012–13 season. Reports indicated, however, that Yakupov would instead return to Russia and play for HC Neftekhimik Nizhnekamsk of the Kontinental Hockey League (KHL). Yakupov had played for the organization previously as a member of its junior teams. His first game with the team was on 22 September against Traktor Chelyabinsk. After two games with Neftekhimik, Yakupov was suspended temporarily by the KHL, as the International Ice Hockey Federation (IIHF) declared that he was not eligible to play in the league. According to IIHF rules, players moving between teams in different countries need to have a transfer card signed by the outgoing national ice hockey federation and the incoming federation. Hockey Canada, the governing body of ice hockey in Canada, had not signed Yakupov's card, making him ineligible to play in Russia. That required him to return to Canada and play with Sarnia for the remainder of the season. The reason they stated was that Yakupov had signed an entry-level contract with the Oilers, and according to an NHL–CHL agreement, players who sign such contracts have to either play in the NHL or for their CHL teams. Due to the NHL lockout, Yakupov could not play in the NHL and was therefore required to play in Sarnia. Within a few days, however, Hockey Canada decided that Yakupov was free to return to Russia, and signed his card; they "determined that Yakupov had no independent legal advice when, at the age of 17 years, he signed his contract with Sarnia."

Yakupov was part of the 2012 World Junior Ice Hockey Championships, joining Russia. His team defeated Canada in the semi-finals, but lost 1–0 to Sweden in the gold medal game, acquiring a silver medal.

On 3 February 2011, Yakupov was named the 'Kal Tire OHL Rookie of the Month' for January, which he had previously won in October 2010. He later won the title for the month of February as well. At the end of the season, Yakupov was named winner of the Emms Family Award as OHL Rookie of the Year, becoming the first Sting player to receive the honour. He was also named to the first All-Rookie team for the season. On 28 May, he was also awarded the title for CHL Rookie of the Year, as the top rookie in the Canadian junior circuit.

On 28 February 2011, at 3:07 in the first period of a game against the Sault Ste. Marie Greyhounds, Yakupov scored his 43rd goal of the 2010–11 OHL season, giving him the new goal-scoring record for a rookie for the Sarnia Sting. On 19 March 2011, in Sarnia's last game of the 2010–11 season, he scored an assist on the first goal as well as the third goal for Sarnia to obtain his 100th point of the season; he also scored another assist with 80 seconds left in the game to finish the season with 101 points.

Early in the 2011–12 season, Yakupov took the scoring lead with 25 points in 10 games. A 12-point week landed him CHL Player of the Week honours for the first time on 18 October 2011.

Yakupov was part of Team Russia in the 2011 World Junior U18 championship. He scored a hat trick in the bronze-medal game, including an empty-net goal with four seconds left, helping defeat Team Canada (with Sting teammate Brett Ritchie) 6–4.

Yakupov was selected second overall by the Sarnia Sting in the 2010 Canadian Hockey League (CHL) Import Draft. Prior to this, he played in the Russian Minor Hockey League (MHL) for his hometown team, Reaktor Nizhnekamsk, but thought that trying to join the Ontario Hockey League (OHL) would be a quicker path to his dream to play in the National Hockey League (NHL).

Yakupov scored his first OHL goal against the Windsor Spitfires on 24 September 2010. After winning OHL Rookie of the Month for the month of October, Yakupov participated in the 11 November game of the Subway Super Series for Team Russia, at the John Labatt Centre in London, Ontario; Russia lost the game 4–0.

Nail Railovich Yakupov (Russian: Наиль Раилович Якупов , Tatar: Cyrillic Наил Раил улы Якупов , Latin Nail Rail ulı Yaqupov; born 6 October 1993) is a Russian professional ice hockey forward who is currently playing with SKA Saint Petersburg in the Kontinental Hockey League (KHL). He was selected first overall by the Edmonton Oilers at the 2012 NHL Entry Draft, and also played with the St. Louis Blues and Colorado Avalanche. Yakupov grew up within the HC Neftekhimik Nizhnekamsk junior program and moved to North America in 2010 to further his career. He joined the Sarnia Sting, a major junior team in the Ontario Hockey League (OHL), where he played for two years before being selected in the NHL Entry Draft. Yakupov played for the Russian national junior team, winning medals in all three tournaments he participated in.