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.[1][2]
Woolpert got his start as a scout and video coordinator for the Seattle SuperSonics in 1986, remaining in the role until 1994.[1] From 1995 to 2004, Woolpert served as a scout for the Portland Trail Blazers. Woolpert also coached in other capacities while maintaining those responsibilities, spending time as an assistant coach with the Sioux Falls Skyforce and the Yakima Sun Kings. Woolpert was promoted to head coach of the Sun Kings prior to the 1998 season, winning his first CBA Championship in 2000. Yakima enjoyed continued success with Woolpert at the helm, winning the CBA Championship in 2006 and 2007, while setting a CBA record for winning percentage, finishing the 2007–08 season with a 43–5 record (.895).
After serving as head coach of the Tulsa 66ers in 2008–09, Woolpert moved to Australia where he spent two seasons as the head coach of the Townsville Crocodiles.[3]
In 2014–15, Woolpert served as the Perth Wildcats' lead assistant coach.[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.[7] The SunKings went on to win NAPB championship in 2018.[8] In 2019, Woolpert led the SunKings to the championships series, where he was released mid series by the owner following a Facebook post made by Woolpert asking for funds to bring his entire roster to the final championship game.[9]
In July 2019, Woolpert was reappointed as lead assistant of the Perth Wildcats.[10] However, he parted ways with the Wildcats on October 23, 2019, to return to the United States for family reasons.[11]
