Dillard played catcher at Saltillo High School in Saltillo, Mississippi. After his senior year, he was selected by the Milwaukee Brewers in the 15th round (448th overall) of the 2001 Major League Baseball draft. Having recently undergone left shoulder surgery, his hitting was not as proficient as Brewers expected, so he instead attended Itawamba Community College in Fulton, Mississippi. In the 2002 draft, he was selected again by the Brewers, this time in the 34th round as the 1,009th overall pick. Dillard signed with the Brewers on May 27, 2003. Rather than continue his catching career, the Brewers informed him that he would be utilized as a pitcher, a position he had only occasionally played in high school.\n', '

Dillard began his professional career in 2003, pitching for the Rookie Arizona League Brewers and Helena Brewers. He played in 14 games, made 4 starts, and went 1–2 with a 3.29 ERA. In 2004, Dillard was primarily a reliever for the Class A Beloit Snappers. He went 2–5 in 43 appearances with a 3.94 ERA and was second on the team in saves (10).\n', '

He played for the Class A-Advanced Brevard County Manatees in 2005, making 28 starts, and accumulating a 12–10 record with a 2.48 ERA. He led the league in games started (28), innings pitched (185⅓), complete games (5), and shutouts (2). He also came in second in wins (12) and fifth in strikeouts (128). Dillard was named to the Florida State League postseason All-Star team in recognition of his performance. He was also selected by the Brewers as their Minor League Pitcher of the Year.\n', '

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