Originally, the Colorado Springs Sky Sox were a Class A affiliate of the Chicago White Sox in the Western League from 1950–1958, when the league folded. The Sky Sox's nickname originated with their affiliation with the White Sox.
The Pikes Peak region was without professional baseball for thirty years until 1988, when the Hawaii Islanders of the PCL relocated to Colorado Springs and became the second incarnation of the Sky Sox. From 1988–1992 the Sky Sox were the Triple-A affiliate of the Cleveland Indians. When Denver was awarded a major league franchise for the 1993 season, the new Colorado Rockies arranged for the Sky Sox to become their top farm team. Through the 2008 season, the Sky Sox have been the only Triple-A affiliate of the Rockies.
During their first season, the Sky Sox moved from the old Memorial Field to the brand new Sky Sox Stadium, now known as Security Service Field. The ballpark, on the eastern edge of Colorado Springs, originally cost $3.7 million to build and seats 8,500 spectators. In recent years, the Sky Sox have invested over $8 million on ballpark renovations which included a new video scoreboard, redesigned entrance plaza, new picnic facility and banquet hall. It is the highest professional ballpark in North America; its natural grass field sits at a lofty above sea level.