Welcome back to our 100-part series on the best Dallas Cowboys player to wear every jersey number from No. 0 to No. 99.
Of the first five entries on our list, there were two in which we didn't have to think about things at all, those being No. 0, which has only been worn by one single player in team history, and No. 4, where the obvious call was the man currently wearing it, Dak Prescott.
Nos. 1, 2, and 3 weren't quite as easy, and we've got a bit of a decision to make here at No. 5 as well. But before we get to our choice, here's a quick look at the five players who've donned the digit for America's Team over the years.
- Bryan Anger, P
- Dan Bailey, K
- Brooks Bollinger, QB
- Clint Stoerner, QB
- John Warren, P
Quarterbacks Brooks Bollinger and Clint Stoerner combined to appear in just seven regular-season games for the Cowboys, so they're out, and while punter John Warren outdid both of them combined, playing a dozen games for Dallas over two seasons, this is simply and easily a two-man race between Bryan Anger and Dan Bailey. And make no mistake about it; it was a close race.
Since coming to the Cowboys in 2021, Anger has undoubtedly proven to be one of the top punters in the league, earning two trips to the Pro Bowl and a pair of Second-Team All-Pro selections. Through the 2025 season, his 13,695 total punting yards are already good for the sixth-most in team history, and his 48.9 total yards per punt and 43.3 net yards per punt both rank No. 1 among all Dallas players to ever play the position.
If Anger continues to put up big numbers over the next few years, he could easily find himself in this spot, but for now, we gave the edge to Bailey.
Dan Bailey has scored the third-most points in Dallas Cowboys history
After an incredible senior season at Oklahoma State in 2010, during which he led the entire country in scoring en route to being named a First-Team All-Big 12 selection, the Big 12 Special Teams Player of the Year, a Second-Team All-American, and the Lou Groza Award winner, Bailey went unselected in the 2011 draft but soon after signed with Dallas as a free agent and made an immediate impact.
After winning the starting job in training camp, the Oklahoma City native kicked a game-winning field goal in overtime to knock off the rival San Francisco 49ers in Week 2 and then became just the third rookie in NFL history to make six field goals in a single game in a Week 3 win over the team now known as the Washington Commanders, actually accounting for every single Dallas point in the 18-16 victory.
He went on to make 32 of 37 field goals that season, including 26 in a row during one stretch, and all 39 of his extra-point attempts en route to earning PFWA All-Rookie Team honors. Bailey's best season with the Cowboys came in 2015, when he made a league-best 93.8 percent of his field goals, hitting 30 of 32, and 100 percent of his PATs for the fifth consecutive season to earn a trip to the Pro Bowl and a Second-Team All-Pro selection.
In seven seasons with the Cowboys, Bailey hit 186 of 211 field goals (his makes remain the most in team history) and missed just two extra-point attempts, connecting on 276 of 278. His 834 regular-season points are good for the third-most in team history, trailing only Emmitt Smith (986) and Rafael Septien (874).
After being surprisingly cut ahead of the 2018 season, as the Cowboys moved on to Brett Maher, Bailey closed his career playing three years with the Minnesota Vikings.
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