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This year’s Winter Classic between the Chicago Blackhawks and St. Louis Blues will boast big-name entertainment and a few new wrinkles when the NHL’s outdoor series lands at Wrigley Field on Dec. 31.

The NHL is once again taking a new strategy with one of its tentpole events. The Winter Classic — which has traditionally been contested on New Year’s Day up until this season when the league ...

the Classic Cup on March 2. The step up to 1,800m will suit some but others will be challenged by the trip in what is traditionally the key lead-up race to the city’s most coveted feature ...