He was the head coach of the Yakima Sun Kings in the Continental Basketball Association (CBA) for seven non-consecutive years (1998–2001, 2004–2008).

Woolpert went to Peninsula College in Port Angeles, Washington and later transferred to the University of Portland, where he was a student assistant coach for the men's basketball team.

Woolpert was promoted to head coach of the Sun Kings prior to the 1998 season, winning his first CBA Championship in 2000.

[4] In August 2015, Woolpert was named an assistant coach for the Los Angeles D-fenders of the NBA Development League.

[5][6] In October 2017, Woolpert rejoined the rebooted Yakima SunKings as its head coach and general manager ahead of the 2018 NAPB season.