Nicknamed the "Yak Attack" for his scoring abilities, 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.

[8] 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.

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.

Toronto Maple Leafs general manager Brian Burke said later that Yakupov gave his team the single worst prospect interview he had ever conducted, referring to the player as "uncooperative and sulky".

Burke added that during the draft interview, a fistfight almost developed between Yakupov and John Lilley, Toronto's chief amateur scout.

[16] Reports indicated, however, that Yakupov would instead return to Russia and play for HC Neftekhimik Nizhnekamsk of the Kontinental Hockey League (KHL).

[19] 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.

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 7 October 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.

[26] 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 12 October 2016.

[31][32] Despite gaining KHL interest, Yakupov was determined to continue in the NHL, and on 4 July 2017, he signed a one-year, $875,000 contract with the Colorado Avalanche.

[36] While continuing in the off-season, Yakupov was then traded on by Vityaz just over a month from his initial acquisition, to Amur Khabarovsk in exchange for financial compensation on 14 June 2020.

[37] In the 2020–21 season with Yakupov looking to assume a larger role with Khabarovsk, he tallied just 1 goal and 7 points through 15 games with Amur before he was traded to Division leading Avangard Omsk in exchange for financial considerations on 20 October 2020.

He was unable to return for the remainder of the season after failing to gain medical clearance, however he remained with the team as they claimed the Gagarin Cup.

Yakupov continued his career in the KHL, leaving Nizhnemkamsk in the off-season and securing a one-year contract with Chinese based club, Kunlun Red Star, on 13 August 2024.

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.