The team played in the Pacific Coast League (PCL) and was the Triple-A affiliate of the Milwaukee Brewers (2015–2018), Colorado Rockies (1993–2014), and Cleveland Indians (1988–1992).

The Pikes Peak region was without professional baseball for 30 years until 1988, when the Hawaii Islanders of the PCL relocated to Colorado Springs and became the second incarnation of the Sky Sox.

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.

In later years, the Sky Sox invested over $8 million in ballpark renovations which included a new video scoreboard, redesigned entrance plaza, new picnic facility and banquet hall.

[3] Concurrent with this move, the Rookie Helena Brewers of the Pioneer League relocated to Colorado Springs, operating as the Rocky Mountain Vibes.