Ogletree began attending Georgia Tech in 2016. In 2019, his senior year, he won the Monroe Invitational by two shots with a score of 279 (−1). In August, he won the U.S. Amateur at Pinehurst, defeating John Augenstein of Vanderbilt, 2 and 1, in the championship match. Ogletree was the third Georgia Tech player to win the title, joining Bobby Jones (five times) and Matt Kuchar. By winning the Havemeyer Trophy, he earned exemptions into the 2020 Masters Tournament, U.S. Open and Open Championship. Ogletree was the low amateur at the 2020 Masters.