The La Crosse-based architectural firm Parkinson & Dockendorff designed the original building.

Additions to the school included an auditorium in 1938–1939, a 1950 classroom expansion, a 1955 gymnasium, and a dedicated music department in 1958.

[3] The present Oconomowoc High School was built in the 1960s and originally had a main section of the building housing two gymnasiums, library, small theater and classrooms for art, music, technical education, business education, industrial arts and home economics.

Oconomowoc quarterback Canton Larson scored 8 touchdowns, including a 493-yard performance, combined through the air and on the ground.

[11] The game showcased the best the Wisconsin Little Ten Conference had to offer, with 25 combined All-Conference players.

[16] In current football history, Oconomowoc has not had much success with claiming only one playoff appearance since joining the classic 8.

The Raccoons later lost to Muskego in round one of the WIAA State Tournament 35-0 bringing their overall record to 5-5.

The baseball program has won conference 25 times, including 14 trips to the state tournament.

Bruett, Sean Smith, Pete Schlosser, Bob Anderson, Andy Neary, Luke Nelson, Logan Wonn, Zach Clayton, and Ryan Brennecke.

The Oconomowoc Raccoons volleyball team won the WIAA State Championship against Appleton North on November 6, 2021.

This was the first time in Oconomowoc High School history that the volleyball team won the state championship.

Oconomowoc ended the regular season 35–5, and never lost a set in the sectionals and state playoffs.

[24] Every year the club donates the proceeds from the event to one or more charitable or non-profit organizations, both local and national.

The lunch includes a burger (veggie or regular), a hot dog or brat, chips, a cookie, and a soda.