In 2009, Jenkins and fellow cornerback Orlando Scandrick competed in training camp and in the beginning of the regular season for the starter position.

In week 3 against the Carolina Panthers he registered an interception, which helped him earn the starting job over Scandrick who focused on the slot corner position.

In a playoff loss to the Minnesota Vikings, he was ineffective on two plays, allowing wide receiver Sidney Rice to score 2 touchdowns.

[4] Jenkins finished the 2009 seasons with 5 interceptions (tied for 12th in the NFL), 23 passes defensed, 49 total tackles and was selected as an alternate to the 2009 Pro Bowl.

Jenkins recorded 55 total tackles, 15 passes defensed (led the team), 1 forced fumble, and 1 interception, while starting every game of the season.

Overcoming the injuries, Jenkins managed to have a solid season recording 22 tackles, 10 passes defensed (led the team) and 1 interception.

The presence of Claiborne added yet another talented defensive back for the Cowboys with newly signed free agent Brandon Carr and veteran Orlando Scandrick.

[10] Because of his contract dispute, he decided to rehab his injured right shoulder outside of the team's training facilities, which delayed his recovery time, forcing him to miss all of the 2012 off-season and preseason action.

He signed a one-year contract with the Oakland Raiders on April 8, 2013 as a free agent, after not receiving the kind of deal he was expecting.

[11] He was named the starter at left cornerback and compiled 15 starts (missed one game with a hamstring injury), 75 tackles, 8 passes defensed, and 2 interceptions (tied for the team lead).

On March 5, 2015, Jenkins signed a one-year, $825,000 contract offer to remain with the Buccaneers, allowing him to return to compete to be a starter against Alterraun Verner and Johnthan Banks.