[3] He was named the Kentucky Gatorade Player of the Year as a junior after averaging 25.5 points, 7.6 assists, 6.8 rebounds and 4.4 steals per game.

[10][11] Sources: Sheppard enrolled at the University of Kentucky in June 2023, shortly after graduating from high school.

[18] On April 18, 2024, Sheppard announced that he would declare for the 2024 NBA draft and forego his remaining college eligibility.

[21] Sheppard made his NBA debut on October 23, 2024, in a 110–105 loss to the Charlotte Hornets, scoring 4 points[22] and on January 6, 2025, he was assigned to the Rio Grande Valley Vipers.

[26][27] Sheppard's older sister, Madison, played college basketball at Campbellsville University.