He is a 6'2" (1.88 m) 180 lb (82 kg) guard and played competitively at Chicago's Marshall High School, Northeastern Oklahoma A&M College and the University of Utah.

He played 120 games in the National Basketball Association (NBA) from 1988 to 1991 averaging 5.4 ppg, 2.1 apg and 1.2 rpg in 12.6 mpg.

Upshaw played with the Miami Heat, the Boston Celtics, the Golden State Warriors and with the Dallas Mavericks.

[11] On February 28, 1990, Upshaw signed a season-long contract with the Golden State Warriors and averaged 5.6 points in 23 games.

[15] In the summer of 1992, Upshaw returned to play in the Philippine Basketball Association this time with Shell Rimula X before joining the Fury.

[17] He has served as an assistant coach for the CBA's Gary Steelheads,[18] Quad City Thunder, LaCrosse Bobcats, and the NBDL's Charleston Lowgators.