Deena Chipp was the first Carlisle female athlete to receive first-team all-state honors. The standout shortstop led the Wildcats to the Little Hawkeye Conference title her senior year before receiving the state’s highest honor when all teams played in one class. Chipp was also a three-time first-team all-conference and two-time all-district selection and was named to the senior all-star game. The five-year starter became the first female athlete from CHS to earn an NCAA Division I scholarship, continuing her softball career at the University of Northern Iowa, where she was a three-time all-conference player and hit .413 as a senior. She ranks among several top-10 statistical categories to this day, including her collegiate career batting average of .348, which is third all-time at UNI.
Todd Isley was the 1990 Iowa High School boys class 3A medalist. Isley capped his senior season with the individual state golf title, coming from three strokes behind on the first day to capture the individual championship by two strokes, shooting a 149 (75-74). He was also Little Hawkeye Conference medalist his senior year. Isley went on to play golf at Central College where he served as captain his senior season and was team MVP.
The 1996 state championship softball team entered the season with the ultimate goal in mind: ending the season on a win. They achieved that goal with a 7-0 shutout win over Anamosa in the state finals. They cruised through the 2A state tournament at Harlan Rogers Field in Ft. Dodge, blanking Waukon (2-0), Esterville-Lincoln Central (4-0) and Anamosa. The team finished the season 46-2 overall and also captured the Little Hawkeye Conference title with a perfect 14-0 record. Five seniors led the team to one of the best seasons in Carlisle softball history.