As a junior, he led his team in both passing (1,361) and rushing (886) yards and a 118.61 passer rating before reluctantly switching to wide receiver for his senior season.

Windsor spent the 2009 af2 season with the Rio Grande Valley Dorados after the Arena Football League (AFL) filed for bankruptcy, catching 184 passes for 2,364 yards and 59 TDs in 15 games.

In response to the NFL lockout, Windsor went back to the AFL and signed with the Arizona Rattlers, where he caught 156 passes for 1,830 yards and 36 touchdowns.

[5] Windsor signed a futures contract with the Browns on January 19, 2011, where he spent the preseason catching 5 receptions, 83 yards and a touchdown.

The Rattlers defeated the Philadelphia Soul 48–39, with Windsor earning ArenaBowl XXVI MVP honors with 10 receptions for 145 yards.