He played college football for the South Carolina State Bulldogs and also had stints in the NFL with the Dallas Cowboys and San Diego Chargers.
[2] After graduating from Southwest DeKalb, Oglesby was convinced by coach Buck Godfrey to attend South Carolina State University.
[2] In his first year at the school, he was named second-team All-Mid-Eastern Athletic Conference while playing both placekicker and punter for the South Carolina State Bulldogs.
[2][3][4] Oglesby earned his second consecutive all-conference selection as a sophomore in 1997, being named first-team All-MEAC as a punter after recording 69 punts averaging 39.3 yards each.
[8] The Cardinals' previous kicker, Bill Gramatica, had injured himself celebrating, and so Oglesby was signed as a replacement for the final three games of the season, beating Vitaly Pisetsky for the job.
[8] Oglesby performed better in his second match, making all three of his field goal attempts, each of his three extra points, and a tackle in the 30–7 win over the Carolina Panthers.