In Holliday's inaugural professional season, the Rockies assigned him to their Arizona League affiliate, who finished with a 42–14 record and won the league championship. He played 32 games and assembled 40 hits in 117 at bats for a .342 batting average, collected four doubles, a triple, five home runs and 23 runs batted in (RBI); his home run total placed third in the league. He played 1999 for the Asheville Tourists, batting .264 with 16 home runs and 76 runs scored. With the bases loaded, he was 3-for-9 with one grand slam and 11 RBI. At third base, Holliday turned in an .871 fielding percentage and 57 putouts.