The Rockies promoted Holliday to the Carolina Mudcats of the AA Southern League (SL) in 2002, where he was named a mid-season All-Star. He was named the league's Hitter of the Week on June 27, after collecting nine hits in 24 at bats with one home run and eight RBI. He won the same award on July 18, after scoring seven runs and driving in 10, and a career-best six RBI against Birmingham on July 14. Holliday ended the season with 128 hits in 463 at bats, 10 home runs, and 64 RBI, batting .276 with 79 runs scored and 16 stolen bases. He played for the Mesa Solar Sox of the off-season Arizona Fall League (AFL) in 2002 and 2003, batting .316 with four home runs, 21 RBI and 10 stolen bases in 35 total AFL games. Holliday remained at the AA level for the 2003 season as the everyday left fielder for the Tulsa Drillers of the Texas League, batting .253, 28 doubles, 72 RBI, 132 hits, 45 extra-base hits, and 206 total bases. His 15 outfield assists tied for second in the league. He earned a spot on the USA Baseball team in the Olympic Qualifying Tournament in Panama. They were eliminated from advancing to the 2004 Summer Olympics.