He played college football at William & Mary, and was selected by the Dallas Cowboys in the fourth round of the 2013 NFL draft.

He was also a member of the Cincinnati Bengals, New York Giants, Cleveland Browns, Chicago Bears, New Orleans Saints, Tennessee Titans, Pittsburgh Steelers, Arizona Cardinals, and San Francisco 49ers.

As a senior, he garnered first-team all-league distinction as a cornerback for the third consecutive season, he also earned second-team all-conference honors as a punt returner.

[7] Head coach Jason Garrett named Webb the fourth cornerback on the depth chart to begin the regular season, behind Brandon Carr, Morris Claiborne, and Orlando Scandrick.

[8] He made his professional regular season debut in the Dallas Cowboys’ season-opening 36–31 victory against the New York Giants.

Webb saw an increased snap count in Weeks 9–10 after Morris Claiborne was sidelined due to a hamstring injury.

[9] On December 9, 2013, Webb had a dismal performance and was benched in favor of Sterling Moore during a 45–28 loss at the Chicago Bears in a Week 13.

[11] Webb finished his rookie season in 2013 with 16 combined tackles (13 solo) and one pass deflection in 15 games and zero starts.

[12] Throughout training camp, Webb competed against Sterling Moore, Tyler Patmon, Terrance Mitchell, and Dashaun Phillips to be the fourth cornerback on the depth chart.

[13][14] On August 28, 2014, the Dallas Cowboys waived Webb after he was inactive for their fourth preseason game due to a hip flexor.

[16] Head coach Mike Tomlin named Webb the fifth cornerback on the Steelers’ Depth Chart to begin the season, behind Ike Taylor, Cortez Allen, William Gay, and Brice McCain.

[19] On September 14, 2016, Webb was signed by the New Orleans Saints, to provide depth at the cornerback position after Delvin Breaux suffered a broken fibula.