In 2000, he helped lead Leigh High School a to CCS Championship in a close win over St.

[1] Windsor is best known for winning the Most Outstanding Player award in the 2004 College World Series, pitching for the Cal State Fullerton Titans.

[citation needed] Windsor appeared in just 13 games the rest of 2004, all in relief for Vancouver and Kane County.

[citation needed] Windsor bounced back in 2006 going 4-1 with a 2.97 ERA for Midland, and was soon promoted to AAA Sacramento.

He started again on July 25, but only lasted 2.2 innings, giving up four runs on nine hits and taking the loss, the only decision of his career.