Dillard began his professional career in 1972 playing for the Winston-Salem Red Sox of the Class ACarolina League, with whom he played the entirety of the 1973 season. After recovering from offseason shoulder surgery, Dillard was assigned to the Double-ABristol Red Sox of the Eastern League for 1974. After approximately one month, he was promoted to the Triple-APawtucket Red Sox in the International League. Though having started the 1975 season at Triple-A, more shoulder problems in the first half resulted in a rehab assignment at Double-A. Dillard was called up to the Boston Red Sox in the final week of the season. He made his major league debut on September 28, scoring two runs on two hits and stealing a base. He was a wide-ranging, slick-fielding middle infielder who had quick hands and was above average at turning the double play, but the Red Sox thought they might be able to convert him from a utility player to a second baseman. He began the 1976 campaign with Boston, but was sent down to the Triple-A Rhode Island Red Sox for two months in an attempt to convert him to second, where as he had primarily played as a shortstop up until this time. While in Boston, Dillard became a valuable backup for second baseman Denny Doyle, and eventually for shortstop Rick Burleson and third basemanButch Hobson. Dillard played the entire 1977 season with Boston, but saw little playing time. Across three seasons with the Red Sox, he appeared in 124 games, including 63 at second base, 21 at shortstop, 18 at third base, and 13 as a designated hitter.
Detroit Tigers (1978)
After the Red Sox acquired second baseman Jerry Remy from the California Angels, Dillard was sent to the Detroit Tigers in exchange for two minor leaguers and cash considerations on January 30, 1978. He provided solid support for young infielders Lou Whitaker and Alan Trammell for a full year. He appeared in 54 games, including 41 at second base, for the Tigers in 1978.
Chicago Cubs (1979–1981)
During 1979's spring training, he was traded to the Chicago Cubs for a player to be named later. His most productive season came in his first year at Chicago, when he hit a career-high.283 batting average with five home runs and 31 runs in 89 games played. The following season, he posted career-numbers in games, hits, and RBI. The baseball strike came in 1981, curtailing time of play for everyone, and Dillard's average dropped to.218 in more limited action, though he still amassed 26 hits in 119 at-bats just in 53 games. He played three seasons with the Cubs, appearing in 242 games, including 130 at second and 67 at third.
Dillard was released by the Cubs after the 1981 season, and he later signed as a free agent with the Chicago White Sox for 1982. He played the majority of the season with the Triple-A Edmonton Trappers of the Pacific Coast League, but was called up for 16 games, all at second base, near the season's end. He was released after the season. In an eight-season career, Dillard was a.243 hitter with 13 home runs and 102 RBI in 438 games, including 148 runs, 50 doubles, 6 triples, and 15 stolen bases.
