In 2019, he placed second at the Dan Kolov Memorial and third at the US World Team Trials, and claimed the Bill Farrell Memorial championship and the US National title. Before the COVID-19 outbreak, he placed second at the prestigious 2020 Matteo Pellicone Ranking Series, defeating '14 University World Champion Selahattin Kılıçsallayan and reigning Junior World Champion Erik Arushanian before losing to reigning Asian Games champion Bajrang Punia. Oliver headlined the first major event during the COVID-19 pandemic in the United States, losing to reigning Pan American champion at 79 kilograms Jason Nolf. By the end of the year, he competed at the , where he was upset in the first round by Alec Pantaleo.