Gregory was named to the Division III All-Ohio squad by Ohio Prep Scene and also was named first team All-Ohio in Division III by the Associated Press and the Ohio Football Coaches Association.
Gregory was a three-time all-league and all-district and the county MVP as a senior where he was selected to play in prestigious Ohio North-South All-Star Game and earned South Offensive Player of the Game honors, completing eight of 14 passes for 202 yards and two touchdowns.
Gregory initially signed on to play at Indiana where redshirted his freshman year.
In 2009, Gregory transferred, this time to Kansas State where he soon took over the starting position from Carson Coffman.
In 2011, Gregory was signed as a quarterback for the Tampa Bay Storm of the Arena Football League.