The Penguins haven't won a playoff series since 2018. This year, for the first time in many years, they won't even get the chance.With a victory over Montreal on Wednesday night, the New York Islanders clinched a wild-card spot and eliminated Pittsburgh from the postseason race.It ends the Penguins' run of playoff appearances at 16 years, which was the longest active streak in major North American professional sports.The Stanley Cup playoffs will be held without the Pens for the first time since 2006, when team captain Sidney Crosby was an 18-year-old rookie and the Civic Arena was still standing.The Penguins could have locked up a playoff spot by winning their final two games, but they blew that opportunity with a home loss to the Chicago Blackhawks on Tuesday night."It's not a great feeling," Crosby said after the Chicago game. "I think it's a situation where you just got to make the best of it and prepare the same way today and hope that we get another chance."Thanks to the Islanders, that chance never came.Crosby, Evgeni Malkin, Kris Letang and the Penguins have been a playoff fixture for the better part of two decades. It's a run that's produced three Stanley Cups and likely fast-tracked all three franchise icons to the Hall of Fame. And now, it's finally over.