Oklahoma State hired Cannen Cunningham as an assistant coach on 25 July 2019. On 13 November his brother, Cade Cunningham, committed to the Cowboys. Cade was a 2020 5* PG prospect and played well this season (started 26 games and avg. 20.1 ppg, 6.2 rpg, and 3.5 apg). On 1 April 2021 he declared for the 2021 NBA Draft. Today his brother quit Oklahoma State to manage Cade.