Middleton attended Western Hills High School, where he played as a running back and linebacker.
In his senior season, he posted 1,620 rushing yards and 20 touchdowns, including a 250-yard, 6-touchdown game against Walnut Hills.
Middleton accepted a football scholarship from Indiana University with the plan of being the eventual successor at running back to Anthony Thompson.
A chronic injury to his right ankle that he suffered in the Ohio All-Star game, forced the team to redshirt him in his first season.
As a freshman, because of his size and athletic ability, the coaching staff wanted to find a way to get him on the field and converted him into a cornerback, although his body type was considered heavy for the position.
He was a four-year starter, making 42 starts in 46 games, 245 tackles (18 for loss), 3 sacks, 15 passes defensed, 2 interceptions and one forced fumble.
[6] On July 10, 1996, he signed with the Orlando Predators of the Arena Football League to play wide receiver/defensive back.