Wingard made his debut for Port Adelaide in Round 1, 2012 against St Kilda. In Round 2 against Essendon, he was subbed out of the game with an eye injury but was fine to play the next week. In Round 5 against Adelaide, in the first quarter he received two heavy knocks to the shoulder. His shoulder was strapped and he played the rest of the game but missed the next two weeks. He also missed round 20 against Hawthorn because of a glute injury.
Wingard proved a valuable player in round 22, despite Port Adelaide's loss to the Brisbane Lions, receiving an AFL Rising Star nomination for his 27 disposal, 1 goal and 5 mark performance.
In round 19, 2013, Wingard won the Showdown Medal for his five goal performance. He was described after the match as "Port's most exciting player since Gavin Wanganeen." In only his second season, he averaged 21.3 disposals a game and kicked 43 goals in 2013 and was named in the 2013 All-Australian team, making him the youngest player to make an All-Australian team since Mark Ricciuto in 1994. His 2013 season also saw him rewarded with the John Cahill Medal, making him the youngest player to win a best and fairest at Port Adelaide since Craig Bradley in 1982.
Wingard started the 2014 season brightly, kicking four goals and showing great effort in beating two players to a loose ball to assist captain Travis Boak in the first-ever game at the new Adelaide Oval in round 2, 2014. His efforts greatly helped in guiding the Power to a 55-point win over their local rivals during Showdown XXXVI against Adelaide.