University of North Carolina basketball head coach Dean Smith visited the Spa Catholic gym to sign Cherry in 1988.

Cherry played for the University of North Carolina Tar Heels basketball team under Dean Smith from 1989 to 1993.

[3][5][6] He then spent one season as a women's basketball assistant coach at Middle Tennessee State.

[7][8] Cherry was hired as High Point Men's Basketball Coach on March 26, 2009.

Cherry finished the 11–12 season with a 13–18 record, and High Point ranked 6th in the NCAA in three-point percentage.

The next season, High Point played non-conference games at Wake Forest (L 60–71) and Eastern Kentucky (L 70–73).

Cherry become the winningest coach in the D1 era, passing Bart Lundy, in a 93–69 win over NC Wesleyan on Nov 15, 2015.