Leonard played and started in a total of 89 games at UVA while scoring one goal and 8 assists.
After spending his first year entirely on the bench,[3] Leonard came on strong at the end of 2003, appearing in ten games, including five starts.
He developed into a consistent starter in 2004, and when Joe Franchino went down with an injury, Leonard took his spot at left back; he finished the year with one assist in 22 starts.
Following his retirement from soccer, Leonard graduated from the Stony Brook School of Medicine in 2016.
He later completed his residency in emergency medicine at Stony Brook University Hospital in 2019.