Thomas Woodrey competed at Cooperstown Dreams Park with the West Boynton Gators (FL) during Week 2 in 2006. Thomas and the Gators clinched the Week 2 championship, defeating the Lakeland Rawlings Renegades (FL), 12-0.

A left-handed pitcher, Thomas was a four-year letterman on the diamond for Cardinal Gibbons High School (Ft. Lauderdale, FL). He tallied a total 22 wins throughout his high school career, including a 4-3 record with a 3.15 ERA and 52 strikeouts his junior year (2011) and a 4-2 record with a 1.94 ERA and 53 strikeouts his senior year (2012). Tomas was a two-time Second Team All-Broward County honoree (2010-2011) and was named First Team All-Broward County in 2012.

After his 2012 high school graduation, Thomas went on to continue his academic and baseball careers at the University of Miami (Coral Gables, FL).