Ranking the five biggest moments from Penguins' outdoor games taken in Boston (Penguins)

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Sidney Crosby scores on Ryan Miller during the shootout to win the Winter Classic on Jan. 1, 2008 at Highmark Stadium in Buffalo, N.Y.

BOSTON -- The Penguins are here in Boston for the 2023 Winter Classic at Fenway Park against the Bruins on Monday, Jan. 2.

It will mark the sixth outdoor game the Penguins have played in and their third Winter Classic. They last played outdoors on Feb. 24, 2019 against the Flyers at Lincoln Financial Field, and last played in the Winter Classic on Jan. 1, 2011 against the Capitals at Acrisure Stadium.

As the Penguins gear up for their next outdoor matchup, let's take a look back at the five biggest -- not the best -- moments from their previous battles out in the elements.

5. BRIAN DUMOULIN, KRIS LETANG LOST TO INJURY ON SAME PLAY
Feb. 24, 2019, Lincoln Financial Field

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In their most recent game outdoors, the Penguins didn't survive the first period with their first defense pairing intact. With under four minutes remaining in the first, Flyers winger Wayne Simmonds applied a hefty check to Brian Dumoulin along the wall that left him down on the ice with what was later diagnosed as a concussion. Rushing to Dumoulin's defense, Kris Letang went after Simmonds as bedlam ensued on the ice, but Letang ended up getting hurt, as well, and wound up missing the remainder of the game.

Olli Maatta was already on the shelf with an injury, so the Penguins were forced to resort to a top pairing of Jack Johnson and Justin Schultz for the remainder of the game. Johnson played a season-high 31:08, while Schultz logged 30:02. Despite a disastrous-on-paper top pairing, the Penguins carried a lead in the third period, but ultimately blew it and lost, 4-3, in overtime.

4. MATT CULLEN SCORES GAME-WINNER, PENGUINS WIN FIRST OUTDOOR GAME IN NEARLY A DECADE
Feb. 25, 2017, Acrisure Stadium

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At the time, it served as nothing more than cushioning the Penguins' lead, but Matt Cullen's third-period goal against the Flyers at Acrisure Stadium in 2017 was the game-winner once it was all said and done.

I'll save you the technical breakdown, but the entire sequence embodied what made Cullen such an effective No. 4 center for the Penguins. Although it might be insignificant now, the Penguins had lost two outdoor games in a row and hadn't won outdoors in front of a home crowd at all by that point. It's fitting that "Dad" Cullen played a big part in making that finally happen.

3. COLBY ARMSTRONG SCORES FIRST-EVER WINTER CLASSIC GOAL
Jan. 1, 2008, Highmark Stadium

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There's the obvious magnitude of scoring the first-ever Winter Classic goal, let alone doing it just 21 seconds into the game like Colby Armstrong did back in 2008 against the Sabres at Highmark Stadium. Never mind the work Sidney Crosby did that played a major part in the puck ending up in the back of the net, this was a massive step toward greatness for the Crosby-era Penguins.

Very young team in a brand new, thrilling environment on a grand stage. And they rose to the occasion right out of the gates.

To this day, Armstrong continues to get a kick out of being the fastest to score in a Winter Classic. 

2. PENGUINS WIN INAUGURAL WINTER CLASSIC ON BACK OF SIDNEY CROSBY
Jan. 1, 2008, Highmark Stadium

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Wet snow flying into his face from every direction? Wet snow unevenly slogging the ice? Game on his stick with the entire hockey world watching? The captain did what he always does: Win.

You just knew he'd finish it off, and he did.

For as dull as shootouts have become today, it's still striking what a spectacle Crosby's shootout-winner in the 2008 Winter Classic was. No moment was -- or ever has been -- too big for Crosby.

This would stand as the biggest moment in any of the Penguins' outdoor games, if not for ...

1. SIDNEY CROSBY TAKES CAREER-ALTERING HIT FROM DAVID STECKEL
Jan. 1, 2011, Acrisure Stadium

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There's always going to be the question of what could have been. In the Penguins' infamous navy blue jersey, Crosby was clipped in the head by Capitals forward David Steckel away from the puck in the 2011 Winter Classic. Perhaps at the peak of his performance, the hit marked the beginning of three concerning seasons in which Crosby played in just 99 regular-season games.

Of course, Crosby eventually made a full recovery and went on to win back-to-back Stanley Cups in 2016 and 2017, but it's impossible not to feel as if the Penguins could have another Cup or two in their pocket if he never dealt with those lingering concussion issues.

It would likely take some sort of double-hat trick from Crosby himself to usurp this hit as the biggest moment in the history of the Penguins' outdoor games.

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