Upshaw is the son of Sabrina and Reggie Upshaw Sr., who played football at Middle Tennessee State University. The younger Reggie Upshaw attended the Baylor School in Chattanooga, Tennessee, where he was a multi-sport athlete, winning a state high jump championship and earning all-state honors in football and basketball as a junior. Playing wide receiver and tight end in football, Upshaw had scholarship offers from Vanderbilt, Middle Tennessee and Louisiana–Lafayette. However, he suffered a broken right foot at the end of his season and another fracture at the beginning of his basketball season, prompting him to focus on basketball in the future. As a senior, Upshaw averaged 22 points, 12 rebounds and three blocks per game on the basketball court. He was considered to be a three-star recruit and received attention from several Division I programs before committing to Middle Tennessee and coach Kermit Davis.
College career
In Upshaw's freshman season, he averaged 6.4 points and 3.5 rebounds per game. As a sophomore, Upshaw averaged 9.9 points and 7.0 rebounds per game. The Blue Raiders finished the season 19–16 and lost in the first round of the CollegeInsider.com Tournament. In his junior season, Upshaw was named to the All-Conference USA third team. Middle Tennessee won the Conference USA tournament, defeating Old Dominion 55–53 in the final. Upshaw, who scored nine points in the championship game including the final four points, was named Most Valuable Player. In the NCAA Tournament, the Blue Raiders were given a 15 seed and matched up with 2 seed Tom Izzo-coached Michigan State. In one of the biggest surprises in the history of the NCAA Tournament, the Blue Raiders beat the highly touted Spartans 90–81, with a strong performance by Upshaw, who scored 21 points as his team's top scorer. It was Middle Tennessee's first NCAA Tournament win since 1989. In the following round, however, they lost by 25 points against Syracuse, with Upshaw shooting 1-for-10 and dishing out one assist. Upshaw averaged 13.7 points, 8.5 rebounds and 2.2 assists per game as a junior. After the season, he underwent wrist surgery. As a senior at Middle Tennessee, Upshaw averaged 14.5 points and 6.8 rebounds per game. Upshaw was named to the All-Conference USA second team. Alongside JaCorey Williams, he led the Blue Raiders to the NCAA Tournament again. As a #12 seed, the Blue Raiders earned a first-round win against #5 seed Minnesota. In a game in which Middle Tennessee was the betting favorite despite its lower seed, the Blue Raiders won 81–72 behind a game-high 19 points from Upshaw. In the next round, the Blue Raiders fell to Butler 74–65. Upshaw was selected to play in the 2017 Reese's College All-Star Game.
Professional career
After going undrafted in the 2017 NBA draft, Upshaw signed a free agent deal with the Milwaukee Bucks and played for the team in the NBA Summer League. Instead of joining their training camp in the hopes of making the regular-season roster, he agreed to a ten-month deal with Tigers Tübingen of the German Basketball Bundesliga in mid-July. Regarding the Bucks, Upshaw said, "I didn't feel like the contract that I had with them would have been the best one for me my first year." Upshaw averaged 14.4 points, 6.7 rebounds, and 2.2 assists per game as a rookie. “The amount of work I’ve put in during my first season and this summer have prepared me to take the next step in my career,” he said. For the 2018 NBA Summer League, Upshaw signed with the Los Angeles Clippers. He contributed 24 points, nine rebounds, two assists and a steal in an 89–74 victory over the Washington Wizards on July 11. On July 27, 2018, he signed with BC Andorra of the Spanish Liga ACB. On July 30, 2019, he has signed with Grissin Bon Reggio Emilia of the Italian Lega Basket Serie A.
