Education
Winters graduated from Bellarmine Preparatory School. He attended the University of Portland, playing on the men’s soccer team from 1996 to 1999.
Winters graduated from Bellarmine Preparatory School. He attended the University of Portland, playing on the men’s soccer team from 1996 to 1999.
In the summer of 1999, he also played for the Willamette Valley Firebirds of the USL Premier Development League. In February 2000, the Columbus Crew selected Winters in the third round (33rd overall) of the 2000 Master of Library Science SuperDraft. The Crew released him during the pre-season and Winters signed with the Minnesota Thunder of the USL A-League.
In 2001, he returned to Portland when he joined the Portland Timbers, playing for them until 2005.
In 1999, Winters earned ten caps with the United States men"s national under-23 soccer team as they took third at the 1999 Pan American Games.