And, of course, this time they were playing for the Stanley Cup and not just pretending.
"That was a dream come true for us out there," said Andrew Newton, 24, who grew up a few blocks from Crosby and played on his right wing for seven years. "You grow up and pretend to play for the Cup and now here you are playing for it, kind of. It's ridiculous. It's definitely awesome."
Crosby brought the Cup back home Friday and the local newspaper, The Chronicle Herald, estimated that 75,000 people came out to see it. Only eight of them actually got to lift it and skate around with it.
As part of the planning for Friday's festivities, Crosby called up some of his old road hockey buddies and asked them to partake in a pick-up game with two 20-minute periods. Crosby's team won, 7-3, but he jokingly disputed one of the goals and said if there was a review it would not have been allowed.
"You don't say no when you get a chance to play for the Cup," Newton said. "He contacted just a small group of us, the guys that played roller hockey and ice hockey with him over the years, and we just had the time of our lives. How could you ask for more than this?"
Newton recently graduated from Dalhousie University in Halifax with his engineering degree. Others have gone on to work in different fields. Crosby's close friend Mike Chiasson used to play in the QMJHL.
Crosby, who earned the win between the pipes, said nobody has changed and that's why the game felt like it always did.
"I grew up with these guys and we played the exact same way we did today since we were five or six years old and we had our parents watching us," Crosby said. "You can ask them. The group was the same. The guys' personalities are the same. Everyone has kind of gone their separate ways and gone their own paths in life, but today felt like it did 10 years ago.
"I'm glad I could share that because, really, we probably played for the Stanley Cup 500 times whether it was in the snow, rain or darkness and today was a chance to do it for the real thing. Hopefully it's not our last shot."
Newton said Crosby always had to play goal when they were growing up because "he was so good that the teams would never be fair." However, after putting him in the nets for a few years they started to realize he was getting pretty good there, too.
He showed his prowess Friday by making a few dazzling saves, including one when he went down on his right hip and stacked his leg pads. He also stoned Newton on a breakaway.
"He's hard to score on," Newton said.
Crosby, though, admitted he was using oversized, illegal equipment. Hey, the Penguins don't need this guy getting hurt in a road hockey game.
"I think every kid is attracted to goalie equipment for some reason, but within my first year of playing I decided I wanted to play out," Crosby said. "I think it was a pretty wise decision."
Crosby would like to duplicate Friday's game sometime down the road, and you know his buddies will be there again to play for hockey's Holy Grail.
"You don't know how success is going to affect somebody, but with him, he's just the same guy," Newton said. "No matter how big he gets, how many trophies he wins, he's just the same Sid. That's what makes him so special."
Contact Dan Rosen at email@example.com