Objective We examined the weight management practices of successful high school wrestlers to contribute meaningful data to the conversations that weight-certifying clinicians and athletic trainers have with athletes at the start of the wrestling season. Understanding how elite athletes navigate weight management can inform safer and more individualized guidance during preseason assessments. Specifically, we sought to determine the proportion of state-qualifying wrestlers who competed at or above their certified minimum weight class. We also quantified the magnitude of weight change from certification to state competition and analyzed seasonal trends in both body weight and body fat percentage over a 20-year period. Design Longitudinal retrospective review. Setting Four Minnesota high schools. Patients or Other Participants State-qualifying wrestlers from 2003 to 2023. Independent Variable State-qualifying weight class. Main Outcome Measure(s) Dependent variables are certification weight, measured body fat percent, and calculated minimum weight class. Results Only 48 wrestlers (52.7%; CI = 42.5%, 63.0%) competed at state in their minimum weight class, while the other 43 competed 1 to 2 weight classes above. Thirty-six wrestlers (39.6%) gained weight over the season. Conclusions Nearly half the successful wrestlers competed in weight classes above their minimum weight, while 5% lost 9% to 18% of their body mass over the wrestling season. This suggests factors other than maximizing individual athletic potential, such as team needs to fill a weight class, influence weight management decisions. Over the 20-year span of the study, trends toward lower measured body fat percentage and lower weight fluctuations suggest influences from sports specialization and year-round training and less emphasis on extreme leanness for competitive advantage. Athletes, in consultation with their coaches and clinicians, should select a competition weight class where they can adequately fuel, train, and recover. This may not be their minimum certified weight class.