As a junior golfer, Holmes competed on the Pepsi Junior Golf Tour and later attended the University of Kentucky in Lexington. While there, he played a key role in leading the team to an SEC title. His amateur accomplishments also include representing the United States in the 2005 Walker Cup. Following that event, Holmes turned professional later the same year.

Professional Career Beginnings and Early Success

Holmes quickly made a name for himself on the PGA Tour. In 2005, he was the medalist at the PGA Tour Qualifying Tournament, securing his tour card. The following year, he tied for 10th place at the Sony Open in Hawaii during his first PGA Tour appearance. That same year, Holmes claimed victory at the FBR Open (now known as the WM Phoenix Open), becoming one of the fastest players in PGA Tour history to earn $1 million in career earnings. That win came in only his fourth PGA Tour start and was his fifth event as a professional golfer.

Continued Performances and Notable Achievements

Despite a significant early triumph, Holmes struggled with consistency. In 2007, he finished the season ranked 118th on the PGA Tour money list. However, he rebounded in 2008 with a second victory at the FBR Open, marking his second PGA Tour title. In the final round of that event, he started with a four-shot lead on the 18th tee and held off a strong challenge from Phil Mickelson to secure the win.

Holmes emerged during a period when several promising rookies, including Bubba Watson and Camilo Villegas, joined the PGA Tour. He became known for his powerful driving ability, regularly hitting drives in excess of 300 yards, which distinguished him among his peers.