He was a Liberal member of the South Australian House of Assembly from the 2014 state election, representing Mitchell until 2018 and Gibson until his defeat in 2022.

Following a Cabinet reshuffle on 28 July 2020, Wingard was appointed the Minister for Infrastructure and Transport, and was sworn in on the following day.

He was the Minister when funding was secured to deliver the tunnel solution for the North South Corridor project in Adelaide.

He later joined Network 10 where he was a sports producer/presenter and was a host and commentator for major events such as the Commonwealth Games, IPL cricket, AFL and the National Basketball League.

[1] Wingard was cleared of misconduct by Premier Steven Marshall following the report of a private investigator after accusations of bullying and intimidatory behavior by Leah Cassidy, chief executive of Sport SA.