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 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.
Professional career
Milwaukee Brewers (2003–2018)
Dillard began his professional career in 2003, pitching for the RookieArizona 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 ABeloit Snappers. He went 2–5 in 43 appearances with a 3.94 ERA and was second on the team in saves. He played for the Class A-AdvancedBrevard 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, innings pitched, complete games, and shutouts. He also came in second in wins and fifth in strikeouts. 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. In 2006, while playing for the Double-AHuntsville Stars, Dillard made 25 starts and 4 relief appearances. In those 29 games, he went 10–7 with a 3.26 ERA. He led the Stars in wins, starts, innings pitched, and came in second in strikeouts. He tied for first in complete games and shutouts with one each. He was also selected as a Southern League mid-season All-Star. in 2008 Dillard reached the Triple-A level in 2007, playing for the Nashville Sounds. He went 8–4 with a 4.74 ERA in 34 games. On November 19, his contract was purchased by the Brewers, protecting him from the Rule 5 draft. He was later optioned back to Nashville on March 15, 2008, where he began the season. On May 23, Dillard was called up to the majors for the first time in his career. He made his major league debut that night against the Washington Nationals, pitching one inning and striking outAaron Boone. He returned to Nashville in late June, but was recalled to Milwaukee that September. He was selected to participate in the Arizona Fall League after the season. He played the majority of the 2009 season with the Nashville Sounds, though he did make two relief appearances with Milwaukee in late July. He was designated for assignment prior to the 2010 season to make room on the Brewers roster for Marco Estrada. He cleared waivers and was assigned to Nashville where he played the entire season. During the 2010 campaign, Dillard completely overhauled his pitching delivery from a traditional over-the-top delivery to a sidearm delivery. He received an invitation to spring training with the Brewers in 2011. He began the season at Nashville, but was recalled by the Brewers on May 13, 2011. He was subsequently optioned to Nashville and recalled twice over the course of the season. He began the 2012 season with Milwaukee, but was outrighted to Nashville on July 11. With a minor league ERA at nearly 10.00, he was reassigned to Double-A Huntsville in late August and elected free agency after the season. Dillard signed a contract with Lancaster Barnstormers of the independent Atlantic League of Professional Baseball for 2013. He pitched in six games before signing a minor league contract with the Brewers on May 4. He was assigned to Triple-A Nashville, where he spent the rest of the season before again electing free agency after the close of the season. Yet again, he signed with Lancaster for the 2014 season, appearing in two games, only to sign with the Brewers on May 1 and be assigned to Double-A Huntsville. He was promoted to Nashville on August 23. Over 8 seasons with the Nashville Sounds, Dillard set the team's career franchise records for wins, innings pitched, and runs allowed. He pitched for the Águilas del Zulia of the Venezuelan Winter League during the 2014–15 offseason. Dillard attended spring training with the Brewers in 2015 and was assigned to the Rookie Helena Brewers in a paper move. He bounced back and forth between Helena's roster and pitching for the Triple-A Colorado Springs Sky Sox for the rest of the season. He elected to become a free agent after the season. In December 2016, he signed a minor league contract with the Brewers. He spent the entire campaign with Colorado Springs, before again electing free agency after the season. He pitched the 2017 season entirely with Colorado Springs, this time concluding the year by resigning a minor league deal on November 4. He was assigned to Colorado Springs for 2018 where he played until becoming a free agent after the season.
Texas Rangers (2019–present)
On December 17, 2018, Dillard signed a minor league contract with the Texas Rangers for 2019, and he was assigned to the Triple-A Nashville Sounds to begin the season. This arrangement allowed Dillard, who resides in Nashville, the opportunity to pitch close to his family. In his second stretch with the Sounds, he set the franchise career records for games pitched and strikeouts while adding to his existing marks for wins and innings pitched. He became a free agent following the 2019 season, but was re-signed to a minor league contract with an invitation to spring training on December 16, 2019.
Personal life
Dillard resides in Nashville, Tennessee, with his family. Off the field, Dillard is known for his social media videos in which he often involves teammates. In early May 2019, Twitter suspended his account for an indeterminate reason.
