His breakout game came during Port Adelaide's round 22, 2012 loss to the Brisbane Lions where he received an AFL Rising Star nomination for his 27 disposal, 1 goal and 5 mark performance.

[13] Wingard's 2013 season also saw him win the Showdown Medal for his five-goal performance in round 19 against the Adelaide Crows where he was described after the match as "Port's most exciting player since Gavin Wanganeen.

"[14] At season's end, he was 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.

He won the Mark of the Year in round 12 against St Kilda by jumping high on the shoulders of Sean Dempster.

Wingard also averaged 19.2 disposals a game and was recognised with the All-Australian selection, a stunning achievement for a player having completed just his fourth year at AFL level.

Wingard has signed a new contract at Hawthorn for 2024 even though he will spend most of 2024 in rehab after rupturing his Achilles tendon in round 22 of the 2023.