He played college football for the Texas Longhorns and signed with the Oakland Raiders as an undrafted free agent in 1998.

Dawson played for the Cleveland Browns from 1999 to 2012, and has the second-most field goals made for their franchise, passing Hall of Famer Lou Groza in 2010.

Dawson thought he might have to have season-ending surgery, but he gutted it out, stuck to kicking, and was named as an All-American and the Southwest Region Offensive Player of the Year by SuperPrep.

He is famous for his 1995 game-winning field goal against the University of Virginia, booting a 50-yarder against a 30-MPH wind to give Texas a dramatic 17–16 victory as time expired.

The Cleveland Browns signed Dawson as a free agent in March 1999, and he remained with the team for 14 years until he joined the San Francisco 49ers in 2013.

Dawson kicked the game-winning field goal in the 49ers Wild Card playoff game against the Green Bay Packers on January 5, 2014, giving the 49ers a 23–20 road victory.

[7] He converted four field goals in the game, including the 57-yard game-winner, earning him NFC Special Teams Player of the Week.

On November 18, 2007, Dawson attempted a 51-yard field goal in the closing seconds of the fourth quarter to tie the game against the Baltimore Ravens.

[13] Notably, later in the season on December 16, in the snow and wind gusts up to 40 mph, Dawson kicked another field goal, a 49-yarder which was more improbable, that hit the crossbar.

Hitting this same structure twice in the same season has led some members of the Cleveland press to begin referring to the support post as "The Dawson Bar.

"[14] Prior to the 2008 season, the rule was changed to allow field goal and extra point attempts that hit the uprights or crossbar to be reviewed.

[18] After two seasons and a state title at Lipscomb, Dawson was hired as the head football coach and athletic director at Hyde Park High School in Austin.

[19] On December 5, 2024, Phil Dawson stepped down as the Hyde Park High School Athletic Director and Head Football Coach.

His wife, Shannon, also moved on from her position as the Hyde Park High School Director of Athletic Advancement.