During a three-year span (ages 8–10), Stegall scored 87 touchdowns playing running back, a record still held today.

Because of his speed (he competed on Miami's track and field team where he holds the 3rd fastest 100 meter dash, 10.44 seconds, and 5th fastest 200 meter dash, 21.24 seconds) he was also a dynamic tap dancer, and kick returner, setting a career record of 1,377 kick return yards which lasted until 2002, beaten by defensive back Milt Bowen, who like Stegall signed with the Cincinnati Bengals after college.

In the 1995 season, he was signed as a free agent by the Green Bay Packers, but was a late cut after a serious knee injury during the final days of training camp.

Stegall flourished as a slotback, where in the CFL a player is allowed a running start before the play to gain momentum, being able to outrun defenders with his impressive speed.

Amidst endless offensive coordinator changes, as well as many head coach changes, Stegall still remained a reliable, and at times unstoppable force for the Blue Bombers.

In the 5th game of the Bombers' 2007 season, July 27, 2007, Milt Stegall became the all-time CFL touchdown leader on a 1-yard pass originally designed as a running play for the occasion, surpassing running backs Mike Pringle and George Reed, and went on to score another major before the end of the game to bring his total up to that point to 139 touchdowns.

[2][3][4] On September 12, 2008, Stegall initially tied Allen Pitts with a 16-yard touchdown reception to become the CFL's all-time leader in career receiving yards.

Shortly thereafter, Stegall surpassed Pitts with a highlight reel 92-yard touchdown catch and run, totaling 14,982 yards in his career.

Stegall made it clear one of the conditions he would hold off retirement and return to playing was if his wife gave birth to their second son in Winnipeg.

[12] On July 20, 2006, Milt Stegall scored the winning 100-yard touchdown reception to lead the Blue Bombers to a 25–22 victory over the Edmonton Eskimos with no time left.

On December 12, 2006, Stegall signed a one-year contract extension to stay with Winnipeg for the 2007 season, but indicated that "there's basically no chance" that he will return beyond 2007.

On September 12, 2008, Milt Stegall became the leader in receiving yards, moving past Allen Pitts' previous record.