Oakley led the Hobart squash team with a 3-0 record at the College Squash Association Team Championships' Conroy Cup. The Statesmen finished in second place, after being edged by Wesleyan in the championship match. Oakley posted an 11-5, 11-5, 11-5 victory in the first round match, an 8-1 win over Connecticut College. He posted an 11-1, 11-7, 11-5 win at the top spot in a 5-4 triumph over Tufts in the semifinals. In the championship match, Oakley defeated his Wesleyan opponent 11-5, 11-1, 11-2. Oakley shared a team-high with 11 wins this season.