The Jets originally announced in 2013 that they had reached an agreement with the NHL to host the game, to celebrate five years since the Atlanta Thrashers moved to Winnipeg, returning the NHL to Manitoba after a fifteen-year absence. The team had originally wanted to host the game in 2015–16, its actual fifth season. However, a disagreement occurred between the NHL and the Winnipeg Blue Bombers over the game's exact date: the league wanted it held in December 2015 while the football team became concerned that this date was too close to the 103rd Grey Cup being held at the stadium on November 29. In January 2015, the Jets announced that they could not reach an agreement to finalize a date for the Heritage Classic during the 2015-16 season. On March 6, 2016, the NHL officially announced that the Jets would host the Oilers in the 2016 Heritage Classic during the 2016–17 NHL season; the Blue Bombers would be on a bye week that week and would play their second last home game before the Heritage Classic on October 8. This gave the NHL nearly two weeks to prepare the stadium for the game.
Due to concern over the glare of sunlight expressed by the players, the game was delayed two hours from the original start time of 2:00 p.m. The temperature at opening face-off was 10.1 °C (50.2 °F), which was above seasonal for late October weather in Winnipeg. The Oilers basically controlled the entire game, with three different players scoring goals in the second period, while goalie Cam Talbot made 31 saves in the shutout.
Gameplay during the 2016 Heritage Classic Alumni Game with the Edmonton Oilers Alumni taking on the host Winnipeg Jets Alumni
The Alumni Game preceding the Heritage Classic game featured players from the previous Winnipeg Jets, making it the first time that the current Jets franchise has recognized the original Jets as part of its history other than in name.
Jennifer Hanson, who sang the Canadian National Anthem before Winnipeg Jets games in the 1990s, returned to Winnipeg to sing O Canada prior to the alumni game.
Willy Lindstrom was traded from the Oilers alumni to the Jets alumni prior to the start of the third period in exchange for a first-round selection in the next alumni game. (Lindstrom had previously played for both the Winnipeg Jets and the Oilers during his playing career.) Winnipeg won the Alumni Game 6-5, the winning goal coming from Selanne on a penalty shot with 3.6 seconds left after being tripped by Oiler and Hockey Night in Canada analyst Craig Simpson.