The NHL Alumni Showdown coaches were named on July 26, 2012. Former Red Wings coach Scotty Bowman along with assistant Barry Smith were to coach the Red Wings' alumni team. The pair of Bowman and Smith coached three Stanley Cup wins in Detroit. Former Maple Leaf coach Pat Quinn was to coach the Maple Leafs' alumni team, along with Red Kelly, Hall of Fame player and former Maple Leafs' coach.
On November 2, 2012, the NHL cancelled the game due to the 2012–13 NHL lockout. The date for the cancellation came as a result of a deadline in the league's contract with Michigan Stadium, in which the league would have incurred additional expenses if they cancelled after November 2. 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. The NHL then officially announced the game on April 7, 2013.
The event will be the first Winter Classic to hold events in two locations. The Winter Classic game itself will be held at Michigan Stadium in Ann Arbor, Michigan, the highest capacity non-motorsports stadium in North America. Another rink is to be constructed at Comerica Park in Detroit and will host the Hockeytown Winter Festival and the NHL Alumni Showdown. The Winter Classic game itself marks the first time a stadium dedicated solely to college football would have hosted the Winter Classic (all five previous events were held at Major League Baseball and National Football League stadiums; Heinz Field, the site of the 2011 classic, hosts both college and professional football). The game will return to its customary January 1 date after being played on January 2 in 2012.
The Red Wings-Maple Leafs matchup, an Original Six era rivalry, is the first time an American team and a Canadian team have faced each other in an outdoor NHL game and the first time a Canadian team has played in the Winter Classic (prior to this, the Winter Classic was reserved for American teams and the Heritage Classic for Canadian ones). The unexpected high television viewership from the 2011 Stanley Cup Finals (which featured a Canadian team, 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 American teams; it was this reconsideration that prompted the idea of an international Winter Classic. Because of a divisional realignment that took effect during the preceding offseason, the Red Wings and Maple Leafs are also now division rivals; both teams were placed in the new incarnation of the Atlantic Division, which was renamed from the Northeast Division (the old Atlantic Division became the Metropolitan Division). Had the Winter Classic been played in 2013 it would have been the only meeting between the teams, as both were in separate conferences at the time (as division rivals, they will meet 4-5 times a year, ultimately playing 30 times over a seven-year period).
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. Gleason made his Leafs debut on January 7, 2014. Liles scored against his former team two days after Gleason's debut in a 6-1 Carolina win.
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. The 3.57 million average viewers for CBC's broadcast in Canada was the largest audience ever for an NHL regular-season game in Canadian broadcast history. The game garnered a 2.5 rating, tying the 2009 NHL Winter Classic as the highest-rated NHL regular-season game since 1975. The rating and viewership for the game were up 19% and 18%, respectively, compared to the 2012 NHL Winter Classic.
Comerica Park served as the venue for the 2013 Hockeytown Winter Festival, a two-week event that took place in Detroit leading up to the 2014 NHL Winter Classic. As part of this event, on December 27–28, the 2013 Great Lakes Invitational four-game tournament was held, with Western Michigan emerging as champion over in-state rival Michigan Tech. 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. These were the first outdoor regular-season games for the OHL. The Spitfires won the first game 6–5, while a shootout was required for the second game, with the Whalers getting the 2–1 win. On December 30, in front of 20,337 fans, the AHL affiliates of the Detroit Red Wings and the Toronto Maples Leafs, the Grand Rapids Griffins and the Toronto Marlies played to a shootout, with the Marlies holding the 4–3 edge. This was the seventh outdoor AHL game.
As part of the Hockeytown Winter Festival, two consecutive alumni games were played between former players of the Red Wings and the Maples Leafs on December 31. The Detroit Red Wings swept the doubleheader, winning the first alumni game 5–4, and the second alumni game 6–5, following a shootout, in front of 33,425 in attendance at Comerica Park.
In the first alumni game of the doubleheader, Jiri Fischer scored the first goal of the game on a pass from Jason Woolley just 1 minute, 20 seconds into the game. Less than one minute later, Kevin Miller's goal gave the Red Wings a 2–0 lead. The Leafs then got goals from Stew Gavin and Todd Warriner, to tie the game at 2–2. 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.
In the second period, Pat Verbeek's goal from Miller and Mathieu Schneider gave the Red Wings a 4–2 lead with 15:40 left in the second. 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. The Leafs pulled their goalie for the extra attacker with a minute left. Then, Red Wings coach Scotty Bowman sent 74-year-old Red Berenson, Michigan's head coach, to take the face off with 14.3 seconds left. Berenson was one of two players who participated in the Alumni Showdown who actually started his NHL career in the Original Six era. The other was 68-year-old center Mike Walton, who began his career with the Leafs in 1965.