Dawson was born on a United States military base in Freising, Germany. He attended Florida Southern College, graduating in 1985, when turned professional. Dawson has enjoyed a long career playing both the PGA and Web.com Tours. He played on the PGA Tour in 1991–1997, 2000–2001, 2003–2008 and 2012 and played on the Web.com Tour in 1990, 1999, 2002, 2009–11, and 2013.
Dawson has won once on the Web.com Tour, a three stroke victory at the 2002 LaSalle Bank Open. His best finish on the PGA Tour is 2nd at the 1995 Greater Milwaukee Open, when he finished three strokes behind Scott Hoch.
In 2003, Dawson became involved in two separate incidents involving rules breaches. At the Chrysler Classic of Tucson in March, he was playing with Brandel Chamblee when Chamblee took an incorrect drop. Dawson was criticized for only notifying rules officials shortly after he had signed Chamblee's card, meaning disqualification rather than a two-stroke penalty.[2] In a similar incident in October, Dawson was playing with Esteban Toledo when he called Toledo on an incorrect drop, resulting in Toledo's disqualification. The latter incident resulted in a feud in which Toledo sacked the agent both players shared, and Dawson was eventually fined $10,000 for not informing officials of an infringement promptly.[3]