Upshaw played with the Miami Heat, the Boston Celtics, the Golden State Warriors and with the Dallas Mavericks. He also played professionally in Stargard Szczeciński, Poland (Komfort Stargard Szczec), Italy (Scavolini Pesaro), Argentina, Philippines, and in the CBA with the Quad City Thunder, Albany Patroons, Rapid City and Jacksonville Jets. He was selected in the second round of the 1986 CBA Draft by the Jets.\n', '

After spending the 1986–1987 season with the Jacksonville (later Mississippi) Jets, Upshaw signed with the West Palm Beach Stingrays of the USBL in the spring of 1987. The Jets cut Upshaw on May 26, 1987 due to injury but recalled Upshaw in late June. Upshaw returned to the Mississippi Jets later in 1987 and was selected to the 1988 CBA All-Star Game. Upshaw later played for the CBA\'s Rapid City Thrillers for the rest of the season.\n', '

Upshaw signed with the Palm Beach Stingrays in June 1988. Upshaw then played for the CBA\'s Albany Patroons for most of the 1988–1989 season. In January 1989, Upshaw signed with the NBA\'s Miami Heat. In two ten-day contracts with the Heat, Upshaw played in nine games and averaged 6.8 points, 1.5 rebounds, 3.7 assists. Upshaw re-joined the Patroons on February 7. The NBA\'s Boston Celtics signed Upshaw in March 1989 to relieve the injured Ramón Rivas. Upshaw played in 23 games for the Celtics averaging 6.3 points, 1.4 rebounds, and 2.2 assists. The Boston Globe noted at the time, "Upshaw has brought to Boston instant up-tempo offense along with tough, chest-to-chest defense against some of the league\'s best (Isiah Thomas, Mo Cheeks), as well as a certain sang froid in delivering the big jumper."\n', '

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