Tobey committed to UVA over schools such as Maryland, Pittsburgh, and Xavier. During his time at Virginia, he split time between being a starter and being one of the first substitutes off the bench. His play off the bench earned him the ACC Sixth Man of the Year award in 2015. Tobey was on the United States national under-19 basketball team that won the 2013 FIBA Under-19 World Championship. Tobey ended his collegiate career as Virginia's all-time leader in games played, appearing in 138 games over his four years.