He has the second highest field goal accuracy of any kicker in NFL history. Bailey was the most accurate kicker in 2015, tied with New York Giants placekicker Josh Brown, with 93.8% converted and 100% of extra points converted.
Born in Oklahoma City, Bailey grew up in Mustang, Oklahoma, and attended Southwest Covenant School where he was an all-state, all-conference kicker and a first-team all-city punter (as selected by The Oklahoman), while playing eight-man football.
As a senior, Bailey had 51 touchbacks in 61 kickoffs. He holds the high school state records for longest field goal (50-yards), most field goals in a season (seven) and career (14). He was also an individual state champion golfer. Bailey graduated from Southwest Covenant as valedictorian of the class of 2007.
Bailey originally accepted to walk on at University of Arkansas, in order to receive an academic scholarship that would cover his tuition. After losing the competition for the starting kicker job, he was approached by head coach Houston Nutt and told that he would have to pay his own way, so he wouldn't count toward the team's scholarship limit. Forced to leave the school, he spent one year out of college before walking on at Oklahoma State University.
As a true freshman in 2007, Bailey made 20-of-20 extra point kicks but only two-of-four field goals. Bailey made field goals from 27 and 28-yards and missed two attempts beyond 40-yards.
Until the 2008 Holiday Bowl, Bailey made 10 consecutive field goals in his sophomore year (2008). With a 78.9% field goal conversion rate (15-for-19) on the season, he was second in the Big 12 Conference in field goal percentage. He made a career-long 45-yarder in the 2008 Holiday Bowl, a 42-31 loss to Oregon.
Bailey made 46-of-46 extra point attempts and 13-of-18 field goals in 2009 as a junior. In the October 17 game, a 33-17 win over Missouri, he made 4-of-4 field goals, including a career-long 51-yarder.
In 2010, Bailey made 24-of-28 field goals and 65-of-66 extra points. He won the Lou Groza Award for the nation's top kicker following the season. He earned the Big 12 Special Teams Player of the Year award. Oklahoma State won the December 2010 Alamo Bowl 36-10 over Arizona, and Bailey made three of three field goals in that game: from 40, 50, and 44-yards.
Bailey was signed by the Dallas Cowboys as an undrafted free agent following the 2011 NFL Draft on July 25. At one point during training camp, he had to compete with three other place kickers that included David Buehler, Shayne Graham and Dave Rayner. He was named the team's kicker at the end of the preseason, with Buehler remaining on the roster as the kickoff specialist.
In the second game of the regular season against the San Francisco 49ers after missing a chip shot attempt in the first quarter, he made a 48-yard field goal to send the game into overtime and the eventual game winner from of 19-yards.
In Week 3, an 18–16 win over the Washington Redskins, he tied a rookie record by converting six field goals (accounting for all of Dallas' points). This was the first time since 2001 that the Cowboys won a game without scoring a touchdown and the sixth in club history. He became the third rookie in NFL history to make six field goals in a game. Garo Yepremian made six-of-eight November 13, 1966, for the Detroit Lions, and Jeff Reed made all six on December 1, 2002, for the Pittsburgh Steelers. This performance earned him NFC Special Teams Player of the Week honors.
Bailey would go on to complete one of the best kicking seasons in franchise and league history by a rookie, making 32-of-37 (86.5%) field goals, second-highest kicking percentage for a rookie, setting a Cowboys rookie record for most field goals made in a season (32) and in a game (6), tied Chris Boniol for the second-most consecutive field goals made (26) in club history and was named to the Pro Football Writers Association All-Rookie team.
On November 20 (Week 11), Bailey kicked his first game-winning field goal, a 39-yard kick in overtime to help the Cowboys beat the Redskins 27-24.
Bailey missed a potential game-winning 49-yard field goal during the December 4 (Week 13) game against the Arizona Cardinals. With the game tied at 13 with 6 seconds left in the fourth quarter, Cowboys head coach Jason Garrett called a time-out before the snap, but Bailey's kick was good. Following the time-out, Bailey kicked the field goal short and to the left, leaving many Cowboys fans frustrated, convinced Garrett had just iced his own kicker. In overtime, the Cardinals won 19-13 on a touchdown] by LaRod Stephens-Howling.
On December 11 (Week 14), however, in a game against the New York Giants with the Cowboys trailing 37-34, Bailey's first attempt at a game-tying 47-yard field goal was interrupted when Giants coach Tom Coughlin called a time-out, effectively icing the kicker. Bailey's first kicked ball did go through the uprights. However, Giants defensive end Jason Pierre-Paul blocked Bailey's kick after the Giants timeout.
Bailey converted three field goals with distances of 32, 26, and 22-yards in Week 3 (September 23), a 16-10 win over the Tampa Bay Buccaneers. His last field goal in the game put Dallas up 16-7, a two-possession lead with 2:47 left. Dallas lost the Week 6 (October 14) game 31-29 to the Baltimore Ravens after Bailey missed a last-second 51-yard field goal. With 32 seconds left, Tony Romo completed a four-yard touchdown pass to Dez Bryant, but because the following two-point conversion failed, Bailey had to make an onside kick. Dallas recovered the kick, but his 51-yard field goal attempt sailed wide right with six seconds remaining.
The following game (Week 7, October 21) against the Carolina Panthers, Bailey kicked 28 and 38-yard field goals within the final four minutes in Dallas' 19-14 victory. In the Week 11 (November 18) 23-20 overtime win over the Cleveland Browns, he made the game tying 32-yard field goal with two seconds left in regulation and the winning 38-yard field goal in overtime.
After trailing the Cincinnati Bengals 19-10 with 6:35 left, Dallas beat Cincinnati 20-19 in Week 14 (December 9). The fourth quarter comeback consisted of a touchdown pass from Tony Romo and a last-second 40-yard field goal by Bailey.
In the Week 15 game on December 16 against the Pittsburgh Steelers, Bailey hit a game-winning 21-yard field goal following a 36-yard interception return by Brandon Carr. In overtime, the Cowboys won 27-24. This win kept the Cowboys' postseason hopes alive.
In the final two weeks of the 2012 season, Bailey kicked a field goal in each game, both resulting in losses. The Cowboys would miss the playoffs.
Bailey moved into third place in club history with 77 career field goals, after making two against the Minnesota Vikings. He also set the franchise record for most field goals over 50-yards for a single-season (6) and a career (11).
On January 23, Bailey and the Cowboys agreed on a new seven-year contract. His new contract was reported to be worth $22.5 million with a $4 million signing bonus and a total of $6.6 million in guaranteed money.
On September 21, he set a franchise record with his 28th consecutive field goal, making a 40-yard attempt in the third quarter against the St. Louis Rams.
On October 5, he missed a potential game-winning 53-yard field goal against the Houston Texans at the end of regulation, breaking a franchise record streak of 30 consecutive makes dating back to the previous season. He later kicked the game-winning 49-yard field goal in overtime.
On October 12, Bailey became the most-accurate kicker in NFL history with a 48-yard made field goal in the first quarter of the Cowboy's 30-23 eventual win over the Seattle Seahawks.
Bailey moved into second place in club history with 182 career extra points, passing Mike Clark after making three against the New York Giants in the season opener.
On December 7, he made four of four field goals, including a game-winning 54-yard field goal with seconds remaining, to lift the Cowboys to a 19-16 win over the Washington Redskins on Monday Night Football. This performance earned him his second NFC Special Teams Player of the Week award.
Bailey was selected to his first career Pro Bowl in December, after making a career-high 93.8% of his field goal attempts, including being perfect (19-for-19) from 39-yards or closer. After the NFL decided to move back the extra point distance from the two-yard line to the 15-yard line, he responded by making a perfect mark of 25-of-25.
In the Dallas Cowboy's season opener, Bailey kicked four field goals against the New York Giants. He connected on field goals of 54 and 56-yards. On October 16, he kicked three field goals against the Green Bay Packers. He recorded his 23rd career game with three or more field goals, which is the most in team history. On December 18, he kicked four field goals against the Tampa Bay Buccaneers, but missed two. His misses were the second time he has missed two attempts in a game in his career (last time was 2011).