Ashley was a graduate of Deshler High School in 1995 where he was a four year starter for the Tigers in baseball and was a safety and wide receiver on the Deshler Football Team. In baseball he started as an outfielder on the 1992, 1993 and 1995 Area Champion Baseball Teams for the Tigers and helped lead the 1993 team to the State semifinals. He was selected to the Times Daily All-Area Baseball Team in 1993. 1994 and 1995 along with being named the 1995 Times Daily 4A-6A Player of the Year. Following an outstanding high school baseball career, he was signed to a baseball scholarship by Northwest Shoals Community College where he was a two time All-Conference selection and was an Academic All-American in 1997. Ashley went on from Northwest Shoals to play for the University of Alabama in Huntsville during his junior and senior seasons where he was selected to the All-Gulf South Conference Team and the All-Tournament team in 1998. He also was selected to 1998 NCAA Division II South Central Regional All-Tournament Team.