He followed with 11 goals in 63 games in his second season and 14 in 81 games in his third year, but posted unsightly plus/minus numbers in both of those campaigns, going minus-33 in 2013-14 and minus-35 in 2014-15.
Neither of those Oilers teams were very competitve, but the numbers certainly weren't trending in the right direction.
Following the 2015-16 season, in which he scored eight goals, 23 points and was a minus-16 in 60 games, the Oilers dealt Yakupov to the St. Louis Blues, where he had three goals and nine points in 40 games last season, his only one with the club.
But the offensive upside has always been tantalizing with Yakupov; he scored 80 goals in 107 games over two seasons with the Sarnia Sting of the Ontario Hockey League, rocketing himself to the top of draft boards League-wide.
The Avalanche -- whom the Wild don't play until the day after Thanksgiving -- bought low on the 24-year-old and have so far been rewarded.
It took just four games for Yakupov to match his goal total from last season, and so far, the defensive metrics have been greatly improved as well.
"I've been through a lot of organizations. You play with different guys, you have different coaches, different city. Everything is so different," Yakupov told the team's website. "Here in Colorado is different too, but I think it's a great opportunity for me to kind of start everything on a new page and so far I'm enjoying being here with these guys and with this organization. I want to stick with it."
Yakupov has also brought with him a positive attitude to Denver, a reputation that didn't always precede him in Edmonton and St. Louis.
Of course, when you're producing, and the team is winning, as Colorado (5-4-0) has been doing more consistently early this season, the smiles come a lot more frequently.
"I think he always has a smile on his face, whether he is speaking Russian or English," Avalanche captain Gabriel Landeskog told the team's website. "He's always a funny guy."