Womack's football career began at Phoebus High School in Hampton, Virginia, where he was the first football player in school history to have his number retired. He finished his career as the Virginia Group AAA all-time leading rusher with 5,570 yards and was named the state's top football prospect his senior season.
Womack was the subject of an intense recruiting battle between the University of Virginia and Penn State. He chose Penn State, at first. He then changed his mind and decided he wanted to play for Virginia.
He was initially successful at Virginia, backing up all-time leading rusher Thomas Jones and leading the team in rushing in one game.
However, Womack's personal life slowed down his college football career.
Womack's junior season in 2000 was truly his coming-out party (after a year's layoff). He was outstanding in his first season as the Cavaliers' starter, totaling an ACC-best 1,028 yards and nine touchdowns. He earned first-team All-ACC honors for his efforts and received Virginia's Outstanding Offensive Player Award.
The 2001 season was shaping up to be Womack's best at Virginia. However, in the first quarter of the season opener against Wisconsin, he slipped on the wet artificial turf and sprained his ankle and missed several games. Womack returned later in the year for a game against Georgia Tech and helped spark a Virginia comeback. He also led the Virginia comeback against Penn State in his final collegiate game, rushing for 153 yards on 31 carries.