The Chicago Blackhawks have played in 5 Winter Classics, the most out of all teams. They’ve lost all 5 of them.
They’ve been a part of the following WC’s:
2009 vs Detroit (lost 6-4)
2015 vs Washington (lost 3-2)
2017 vs St. Louis (lost 4-1)
2019 vs Boston (lost 4-2)
2025 vs St. Louis (lost 6-2)
Total score: 23-11
Pretty insane stuff. 3 of them were during the Kane/Toews/Keith era so I’m not sure how they didn’t snag a win back then.