Jackson played college football for the Ohio State Buckeyes, where he alternated with Joe Germaine at the quarterback position.
During his time as a football player, Stanley Jackson would periodically work as a staff member at The Lords Ranch in Warm Springs, Arkansas.
After sitting out all of 2003 with a knee injury, Winnipeg Blue Bombers gave Jackson a chance to play quarterback again in 2004.
[5] After retiring for two years, Jackson played for the Marion Mayhem of the newly formed, Continental Indoor Football League.
[8] In February 2023 Jackson was named as the head football coach at Westerville North High School.