Drafted by the Atlanta Braves in the 6th round of the 2009 MLB Draft from the University of Alabama-Birmingham. Did not sign and in 2010, Woolley was drafted by the Texas Rangers in the 39th round. Decided to stay at UAB for his final season and finally signed in 2011 after being drafted by the Detroit Tigers in the 13th round of the draft.
Started 2011 with the Connecticut Tigers of the New York Penn League and finished with the single-A West Michigan Whitecaps. Woolley posted a combined 1-2 record with a 3.45 ERA in 2011 in 47.0 IP, striking out 44 batters and walking just nine out of the bullpen.
In 2012, Woolley began the year with the Whitecaps before being called up to the single-A Lakeland Flying Tigers of the Florida State League. In 2012, Woolley was 4-2 with a 3.57 ERA in 63.0 IP to go along with 55 strikeouts and 27 walks. In 2013, Woolley was signed by the Atlanta Braves and began the year with the double-A Mississippi Braves, throwing in three games and putting up a 12.27 ERA over 3.2 IP. He was then sent down to the Lynchburg Hillcats, appearing in 15 games with a 6.33 ERA in 21.1 IP.