He played college football for the Arizona State Sun Devils, and was selected by the Cowboys in the second round of the 1992 NFL draft with the 37th overall pick.

[citation needed] A running back and linebacker at Maryvale High School, he earned All-Metro Division AAA and All-City honors as a senior, once scoring six touchdowns in a single game.

[1] According to a January 23, 1996, article in The New York Times, because Woodson failed to meet NCAA academic qualifications for a scholarship, he walked on at Arizona State University.

During his senior year, he showed his great athleticism by lining up during 2 games as a defensive end and playing on several occasions as an inside linebacker.

Head coach Jimmy Johnson named Woodson the backup strong safety to begin the regular season, behind Thomas Everett.

[12] The Dallas Cowboys finished the 1992 NFL season atop the NFC East with a 13–3 record and earned a first round bye.

On January 10, 1993, Woodson appeared in his first career playoff game as the Cowboys defeated the Philadelphia Eagles 34–10 in the NFC Divisional Round.

Head coach Jimmy Johnson named Woodson the backup strong safety to begin the regular season in 1993, behind Everett.

On January 16, 1994, Woodson started his first career playoff game and made seven combined tackles and an interception during the Cowboys' 27–17 win against the Green Bay Packers in the NFC Divisional Round.

[19] On March 29, 1994, Dallas Cowboys' head coach Jimmy Johnson announced his decision to resign due to multiple disagreements with owner Jerry Jones.

[22] On September 11, 1994, Woodson recorded eight combined tackles and made his first career regular season interception during a 20–17 win against the Houston Oilers in Week 2.

Woodson intercepted a pass by Oilers'quarterback Bucky Richardson, that was intended for wide receiver Haywood Jeffires, and returned it for a three-yard gain in the third quarter.

On December 4, 1994, Woodson recorded four combined tackles and returned an interception for his first career touchdown during the Cowboys' 31–19 win at the Philadelphia Eagles in Week 14.

On January 8, 1995, Woodson made five combined tackles as the Cowboys defeated the Green Bay Packers 35–9 in the NFC Divisional Round.

On October 1, 1995, Woodson recorded nine combined tackles, forced a fumble, and returned an interception for a touchdown in the Cowboys' 27–23 loss to the Washington Redskins in Week 5.

Woodson intercepted a pass by Redskins quarterback Gus Frerotte, that was intended for defensive end Tony Woods and returned it for a 37-yard touchdown in the second quarter.

On January 28, 1996, Woodson made ten combined tackles as the Cowboys defeated the Pittsburgh Steelers in Super Bowl XXX.

On December 15, 1996, Woodson recorded six combined tackles, forced a fumble, and made a season-high two interceptions during a 12–6 victory against the New England Patriots in Week 16.

On September 7, 1997, Woodson recorded nine combined tackles, forced two fumbles, and made a sack as the Cowboys lost 25–22 at the Arizona Cardinals in Week 2.

On January 9, 1998, Cowboys head coach Barry Switzer announced his decision to resign stating it was in the best interest of the team after they failed to make the playoffs with a 6–10 record in 1997.

[41] On January 26, 2000, Cowboys owner Jerry Jones officially promoted defensive coordinator Dave Campo to head coach.

In Week 10, Woodson tied his season-high of eight solo tackles, deflected two passes, and made an interception during a 36–3 loss to the Philadelphia Eagles.

Seahawks head coach Mike Holmgren stated Jackson almost died in the locker room as medical personnel struggled to keep his airway open while he was having a seizure for 40 minutes.

On December 7, 2003, Woodson made six solo tackles and a season-high three pass deflections in the Cowboys' 36–10 loss at the Philadelphia Eagles in Week 14.

[57] In February 2011, ESPN.com writer Tim MacMahon wrote that Woodson "deserves serious Hall of Fame consideration and should join the Triplets on the modern side of the Dallas Cowboys Ring of Honor.

[59] The only Cowboys player to suit up for both Jimmy Johnson and Bill Parcells, Woodson had a rare ability to play both the run and the pass.

According to an article from July 3, 2009, on DallasCowboys.com, "While Woodson delivered his share of big-time hits from the safety position, he was always the team's slot cornerback, covering receivers inside, which is considered to be the toughest spot on the field.

"[64] In a December 30, 2004, article published in Knight Ridder newspapers, Clarence Hill described Woodson as "the most versatile safety in the league and arguably the best in (Dallas Cowboys) history."

An October 31, 1994, article in Sports Illustrated described Woodson as "a masher who doubles as an outside linebacker in passing situations" and "the most productive player on the best defense in the NFL."

[67] Woodson has two sons, Darren Jr. and Jaden, and a daughter, Miranda from a previous marriage, and resides in Dallas, where he serves as a board member of Make a Wish Foundation (North Texas).