Grayson Crawford began his college career at Southern Arkansas University before transferring to Stillman College where his father Donny Crawford was the coach. He played catcher for three years at Stillman and graduated in 2010 with a degree in health & physical education.
Immediately after graduation Crawford joined the coaching ranks and did a lot of hopping around over the next dozen years. In fall 2010 he served as an assistant coach at Stillman. He moved to Pensacola State College in 2011 as an assistant coach and stayed through the 2012 season. This two season stint was followed by another two season stint. Crawford took over as head coach of the Christian County High School Colonels for the 2013-2014 seasons. In each season he led his team to the regional championship game and overall compiled a 47-35 record. In addition to coaching responsibilities at Pensacola and Christian County, Crawford spent the 2012-2014 summers as the head coach for the Hoptown Hoppers in the summer collegiate Ohio Valley League. He led the Hoppers to the playoffs each year and won the championship in both 2012 and 2013.
Crawford returned to the college ranks in 2015 as an assistant coach and recruiting coordinator for Lindsey Wilson College. He played an important role in helping the Blue Raiders reach the NAIA World Series for the first time. Continuing to move up the coaching ladder, Crawford spent the next two years at Division I Murray State University. He served as their volunteer assistant coach in 2016 and was promoted to assistant coach in charge of pitchers for the 2017 season.
His next three coaching stops all started in January which is a bit unusual in college coaching. He became an assistant coach responsible for pitching at the University of Louisiana at Monroe in 2018, but left the program at the end of June for personal reasons. In 2019 he started as the Austin Peay State University volunteer assistant coach but served as the interim pitching coach for the last 43 games of the season. In the summer of 2019 Crawford returned to the Hoppers for a fourth season, but only stayed until July 12th. He had been named the Austin Peay pitching coach a few days earlier and decided he needed to focus his efforts at Austin Peay. He stayed at Austin Peay only six months more before moving on to Lipscomb University in 2020. He served as the Lipscomb pitching coach in 2020 and for most of 2021.