Windsor attended Leigh High School in San Jose, California. In 2000, he helped lead Leigh High School a to CCS Championship in a close win over St. Ignatius.

Windsor is best known for winning the Most Outstanding Player award in the 2004 College World Series, pitching for the Cal State Fullerton Titans. The Titans upset Texas, with Windsor pitching a complete game 5-hitter to go along with 10 strikeouts in the final. He finished his senior season with a 13-4 record and a 1.72 ERA. He was drafted in the 3rd round, 97th overall, of the 2004 Major League Baseball Draft.

Windsor appeared in just 13 games the rest of 2004, all in relief for Vancouver and Kane County. He got off to a promising start for in 2005, posting a 3.58 ERA in 10 starts. He was called up and did not fare well, putting up a 5.72 ERA in 11 starts for AA Midland. A shoulder injury shortened his season.

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