It was also the first whose festivities were split between two locations, as the NHL Alumni Showdown and other side events were held on a second rink constructed at Comerica Park in downtown Detroit.

On February 8, 2012, the University of Michigan Board of Regents authorized athletic director Dave Brandon to negotiate a contract with the NHL regarding the Winter Classic.

The unexpectedly high television viewership from the 2011 Stanley Cup Finals (which featured the Vancouver Canucks against the Boston Bruins) prompted the league and NBC to reconsider the conventional wisdom that a contest featuring a Canadian team would not draw as well as two U.S. teams in the United States.

[9][10] During the announcement, NHL Deputy Commissioner Bill Daly stated that the 2014 Winter Classic and associated events would be awarded to Ann Arbor and Detroit and would also feature the Maple Leafs and Red Wings.

Despite taking the warmup and initially being pencilled in as a healthy scratch, John-Michael Liles found out early in the game that he had in fact been traded to the Carolina Hurricanes, alongside Dennis Robertson, for Tim Gleason.

The combined average television viewership for the 2014 NHL Winter Classic on NBC in the U.S., and CBC and RDS in Canada was 8.234 million viewers in North America, becoming the most watched regular season game ever.

The previous highest combined average television viewership was 6.6 million viewers for the 2011 NHL Winter Classic.

The 4.404 million average viewers for NBC's broadcast in the U.S. was the second-largest audience for an NHL regular season game since 1975.

[14] On December 29, two OHL games were played, the first between the Windsor Spitfires and the Saginaw Spirit, and the second between the London Knights and the Plymouth Whalers.

[16] As part of the Hockeytown Winter Festival, two consecutive alumni games were played between former players of the Red Wings and the Maple Leafs on December 31.

Petr Klima then gave the Red Wings a one-goal lead when he scored on a pass from Martin Lapointe with 4:04 left in the first period.

Aaron Ward scored the eventual game-winner from Fischer and Jimmy Carson with 11:50 left before the Maple Leafs mounted a comeback on goals by Brad May, and Tom Fergus who made it a one-goal game with 2:31 remaining in the second period.

[18] Prior to the second alumni game of the doubleheader, former linemates Gordie Howe and Ted Lindsay dropped the first puck in a ceremonial faceoff between former captains Steve Yzerman of the Red Wings and Darryl Sittler of the Maple Leafs.

Vladimir Konstantinov was then helped onto the ice for a rare Russian Five reunion with his former teammates, Sergei Fedorov, Viacheslav Fetisov, Vyacheslav Kozlov and Igor Larionov.

Joe Kocur honored his late Bruise Brother by wearing Bob Probert's number 24 in the second alumni game.