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 MLS SuperDraft.
[1] The Crew released him during the pre-season and Winters signed with the Minnesota Thunder of the USL A-League.
[2] 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.
Winters graduated from Oregon Health Sciences University School of Medicine in 2011.