PITTSBURGH — Conor Sheary was still a high school student when Sidney Crosby was playing for the Stanley Cup in 2009.

He remembers watching every game, never contemplating for even a second that he might line up next to the Penguins captain in another Stanley Cup final seven years later.

"You always want to get there, but you never really envision that, especially an undrafted guy like myself, it's hard to imagine," he said.

Sheary is the unheralded, undrafted 23-year-old playing and producing on Crosby's left wing. He scored the second goal of the Penguins' series-opening win on Monday night after receiving a brilliant feed from the Pittsburgh superstar.

It was the third goal and eighth point of the playoffs for Sheary. The lowest-paid player on the team roster is, for the moment, lining up with the arguably the game's top talent on the biggest stage possible.

Sheary, a five-foot-eight 175-pounder, was undrafted out of the University of Massachusetts-Amherst, where he played for four full seasons. The native of Winchester, Mass., led Pittsburgh's AHL affiliate in scoring before signing a two-year deal with the NHL club last summer.

Most clubs were only offering amateur tryouts. Pittsburgh, Sheary said, was one of the few teams seriously interested in his services.

"I think being overlooked a few times just makes that a little easier for to have that chip on my shoulder," he said.

Sheary started this past regular season back with AHL Wilkes-Barre on a team coached by Mike Sullivan, who later replaced Mike Johnston as the NHL team's head coach.

Sheary was in the Penguins lineup four days after Sullivan's promotion in December. He had a goal and an assist in his second NHL game, much of it spent alongside Crosby, who was surging after a slow start to the season.

The two would play only 67 minutes or so together at even strength in Sheary's 44 NHL games, but something fit and the connection would resume again in the post-season.

In assessing the chemistry between the two, Sullivan pointed to Sheary's quickness, his elusiveness in tight spaces, smarts and instincts as well as his ability to work well in tight spaces.

"These are all areas of Sid's games that I think are his strengths," Sullivan said. "So to have a guy like Conor to play with him that allows him the opportunity to play that give-and-go game, maybe free up some space or create some space for Sid to make a play, in those types of situations. I think their skill sets are complementary."

Late in the first period of Game 1, Crosby raced for a loose puck in the Sharks zone and then fired a backhand pass across the ice to Sheary, who beat netminder Martin Jones.

"He makes it pretty easy to play with him when he finds you all over the ice," said Sheary.

It was quite a high for someone who was passed over by all 30 teams in the draft.

"It's been a pretty surreal and whirlwind year for myself," Sheary said. "And (Monday) night was a pretty special moment."