He played college football for Drake University, and was signed by the Dallas Cowboys as an undrafted free agent in 2002.

He made eight field goals over 50 yards during his career with the Bulldogs, including a PFL-record 62-yarder as a junior in 2000 against San Diego.

[1] Cundiff was brought to the 2002 training camp as an undrafted free agent, and won out over incumbent Tim Seder as the team's kicker.

As a rookie, he won the NFC Special Teams Player of the Week award, after making a 48-yard field goal on the game's final play for a 13–10 victory against the St. Louis Rams.

He tied a then-record seven field goals in a game against the New York Giants on Monday Night Football on September 15, 2003.

He replaced kicker Shaun Suisham, in the hope of providing greater consistency to the Cowboys' special teams.

[2] On February 15, 2006, the Tampa Bay Buccaneers signed Cundiff to a contract, but he was released after kicker Matt Bryant was re-signed.

[4] On November 22, 2006, the New Orleans Saints signed Cundiff as a kickoff specialist, easing the workload of veteran John Carney.

[4] In week 5 of the 2009 NFL season, Cundiff hit the game-winning field goal to help the Browns beat the Buffalo Bills, 6–3.

Cundiff was voted to the 2011 Pro Bowl as the AFC placekicker after successfully completing 26 of 29 field goal attempts and a league-high 40 touchbacks.

Cundiff played at home in the outdoor M&T Bank Stadium and set the record after the instatement of the K-ball rule.

[18] However, Akers performed well enough to keep the starting job, and Cundiff was left off the postseason roster and released 17 days later on January 18, 2013.