The first Limestone Challenge was played in 2023 at George Rogers Clark High School in Winchester and featured 10 teams. Participating Limestone schools included Fleming County (A and B teams), Mason County, Montgomery County, and Robertson County. Competing non-Limestone teams included Berea, East Jessamine, Madison Central, Woodford County, and a team comprised of players from each of those four teams. Limestone League teams competed well in the event as Fleming County's 'A' team finished with a 5-0 record, while Mason County went 4-1 and Robertson County finished 3-2 against non-Limestone League teams. 

The event was a resounding success as all four Limestone League schools who competed went on to qualify quick recall teams for the regional tournament with three - Fleming County, Montgomery County and Robertson County - claiming district championships. 

The 2024 Limestone Challenge was played on Saturday, Nov. 9 at George Rogers Clark High School in Winchester and 14 teams participated. Teams included: Fleming County, George Rogers Clark, Mason County, Montgomery County, Robertson County and Rowan County, while Bardstown, Bellevue, Berea, Estill County, Frankfort Christian Academy, Harrison County, and Madison Central made up the non-Limestone division. Limestone teams fared extremely well in the event with Fleming County finishing 7-0, Rowan County 5-1-1 and Mason County 5-2 against non-Limestone teams. Harrison County and Frankfort Christian Academy each finished 5-2 against Limestone League teams. 

The event continued to build its reputation as a strong warm-up event for Governor's Cup as five teams (Fleming County, George Rogers Clark, Robertson County, Rowan County and Berea) won their districts in Governor's Cup while four more (Mason County, Montgomery County, Harrison County  and Estill County) qualified for region as district runner-up. 

The 2025 edition of the Limestone Challenge featured the largest field in its short history. A total of 16 teams participated in the event on Saturday, Nov. 8 at George Rogers Clark High School in Winchester. Teams included: Bath County, Bourbon County, Fleming County (A and B), George Rogers Clark, Lewis County, Mason County, Montgomery County and Robertson County. The non-Limestone division consisted of Bellevue, East Jessamine, Frankfort Christian, Jackson County, Madison Central, Woodford County. 

Nicholas County, which resurrected its program after a 4-year hiatus, participated as a member of the non-Limestone division. 

Fleming County, Bellevue and Madison Central fared well, finishing 7-1 in the event while George Rogers Clark, Jackson County at Frankfort Christian finished 6-2. 

Once again, the event was a resounding success as five participating schools (Fleming County, Robertson County, George Rogers Clark, Jackson County at Woodford County) won their district in Governor's Cup while four more (Lewis County, Bellevue, Frankfort Christian and Montgomery County) qualified for region as district runners-up.