After a two-year stint in the United States playing college basketball for Kentucky, Wynyard returned to the Australian and New Zealand NBL.

[5] On 15 August 2014, Wynyard signed with the New Zealand Breakers as a non-contracted development player so as to keep his amateur status and his NCAA eligibility.

[7] On 26 January 2015, Wynyard committed to the University of Kentucky Wildcats basketball program with the aim of joining the team in 2016–17.

[5] In October 2015, Wynyard helped Rangitoto College win the Secondary Schools National Championships while earning MVP honours.

[18] In November 2015, Wynyard signed a National Letter of Intent to play college basketball for the Kentucky Wildcats.

[19] He joined the squad in December 2015[18] and redshirted the 2015–16 season in order to retain four full years of college eligibility.

[20] In 2016–17, Wynyard logged a mere 34 minutes in Kentucky's first 20 games, while stuck behind fellow Wildcat big men Edrice Adebayo, Isaac Humphries and Sacha Killeya-Jones.

[49] On 7 December 2024, Wynyard signed with the New Zealand Breakers as an injury replacement player, providing cover in the absence of Dane Pineau and Jonah Bolden.

[1][51][52] He later missed out on making the final squad for the 2014 FIBA Basketball World Cup in Spain but went on to lead the Junior Tall Blacks in December during the Oceania Championships in Fiji.

[53] After helping lead the Tall Blacks to the 2015 Stanković Cup title, Wynyard played in the two-game FIBA Oceania Championship series against Australia.

[58] In April 2023, Wynyard helped New Zealand win bronze at the 3x3 FIBA Asia Cup and earned all-tournament team honours.