And the reunion may be a happy occasion for Galchenyuk, the gifted Canadiens forward who will celebrate his 21st birthday on Thursday when Montreal plays host to the Oilers at the Bell Centre.
The Canadiens (35-15-3) are battling for top spot in the NHL Eastern Conference and Galchenyuk is enjoying a strong season with 15 goals and 35 points in 53 games.
Things have not gone as well for Yakupov, with just six goals and 15 points in 55 contests for Edmonton (15-31-9), mired in last place in the Western Conference.
"We talk quite a bit," Galchenyuk said Wednesday. "I'm happy to play against him."
They were teammates on the Sarnia Sting of the Ontario Hockey League and among the world's top junior prospects in 2012, when the high-scoring Yakupov was drafted first overall by Edmonton and the clever playmaker Galchenyuk went third overall to Montreal.
But for a variety of reasons, Galchenyuk has made steady progress from season to season since entering the NHL in the lockout-shortened 2013 campaign while Yakupov's production has sagged since he led rookie scorers with 17 goals in 48 games the same year.
It helped Galchenyuk to be on a team with veteran leaders that was moving upward in the standings, while Yakupov struggled with a rebuilding team.
The Canadiens managed Galchenyuk's minutes carefully in is first two campaigns, then started giving him regular top-six exposure this season. He has improved with each step.
"It's a process with Alex," said coach Michel Therrien. "We got him at 18 and we wanted to make sure that he understood the game.
"The challenge for a coaching staff with young players is to make sure they don't lose their confidence. We really like the way he's improving every year. He's got more responsibility each year. Time will tell where he ends up but we know we have a good kid who works hard and we want to make sure he reaches his potential."
Galchenyuk was a centre when he was drafted, but has played mostly on left wing in the NHL. Earlier this season, Therrien moved him into the middle for a stretch of games, where he started strong and then went flat.
He's been back on the wing with crafty two-way centre Tomas Plekanec and right winger Brendan Gallagher of late and has picked up his game.
"The coaches have done a great job with all us young guys, but with Chucky (Galchenyuk), they put him in situations where he could succeed from the start," Gallagher said of his linemate. "He did well and the responsibilities came to him. He's handled it well."
Galchenyuk, an American citizen of Belarusian descent, is a slick, six-foot-two stickhandler who also has a quick, hard shot. What his ceiling will be is to be determined, but he looks like a rising star.
The Russian Yakupov has been compared to Pavel Bure for his rocket shot, as he demonstrated in scoring the game-winner in New Jersey on Monday night, but highlights have been rare this season. The Oilers are waiting for more of those, especially with winger Taylor Hall out for six weeks with a leg injury.
The debate on which team got the better player is still to be played out, and Galchenyuk doesn't like to compare.
"I try to focus on myself rather than where we got picked, first or third," he said. "I'm really happy being in Montreal and I'm sure he's happy in Edmonton."