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At the end of every season, the league's coaches vote for the All-WIHLMA Teams. The First Team and the Second Team each consists of three forwards, two defensemen, and a goaltender. In addition, one player from each team is given Honorable Mention.

Beginning in the 2014-2015 season, WIHLMA added All-Academic Teams to honor top students who excel in the classroom and contribute to their varsity program's success. Another new award in the 2014-2015 season, the Harry Rulon-Miller Sportsmanship Award, is to be given yearly to the player from each team who best demonstrates excellence in sportsmanship.

In addition to these individual awards, WIHLMA coaches vote for one team to receive a team award for sportsmanship. In 2014-2015, the league selected Princeton High School as its first annual recipient of the WIHLMA Sportsmanship Award.