Mr. Osborne established himself as a strong athlete even before coming to Episcopal; he scored 43 goals as a freshman on the soccer team at his school in Florida, as well as leading the team in assists – an unheard of combination.
At EHS, he scored 14 goals as a sophomore, 24 goals as a junior, and 18 as a senior. The team set School scoring records in his junior and senior years, including 54 goals in 14 games during his final year at Episcopal. Mr. Osborne co-captained the team his junior year, leading the Maroon to an undefeated record, and captained the team as a senior. During his three years at EHS, the varsity soccer team had a 37-4-4 overall record.
Mr. Osborne was voted to the All-Conference, All-Metro, and All-America (Region 4) teams as a junior. In his senior year, he was selected to the National All-America Team. He received the Peyton S. Hawes III Award for Soccer as a junior and senior.
He also captained the tennis team as a senior, playing No. 2 singles for the team that finished second the league and beat Woodberry for the first time in 17 years. Off the field, Mr. Osborne was elected as a Monitor and member of the Honor Committee. After graduation, Mr. Osborne continued his soccer career at Williams College.