In 2021, Oliver competed at the rescheduled US Olympic Team Trials as the number four seed, in an attempt of representing the United States at the 2020 Summer Olympics. After defeating reigning NCAA champion Nick Lee, Oliver was able to upset reigning Pan American Champion Yianni Diakomihalis and advance to the finale. Next, he faced '18 US Open National champion Joey McKenna, whom he was able to shut down twice to non, becoming the 2020 US Olympic Team Member. As Zain Retherford had failed to qualify the weight for the United States at the 2020 Pan American Olympic Qualification Tournament, Oliver was forced to do so at the 2021 World Olympic Qualification Tournament a month after the US Olympic Trials. At the World Qualification Tournament, Oliver was able to reach the semifinals with wins over Yun Jun-sik, Hor Ohannesian and Ruhan Rasim, however, he was stopped by reigning Individual World Cup champion (70kg) Magomedmurad Gadzhiev, failing to qualify for the 2020 Summer Olympics. As the US Olympic Team Member, Oliver was scheduled to compete at the Pan American Continental Championships from on May 30, however, he was forced to not attend due to a torn LCL sustained at his last tournament, and will be replaced by the runner–up Joey McKenna.