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The hypothesis of this randomized controlled trial was that a clinical decision support system (CDSS) would increase adherence to the Mediterranean diet (MD) among adolescent females with polycystic ovary syndrome (PCOS). The objective was to assess the impact of personalized MD plans delivered via a CDSS on nutritional status and psychological well-being. Forty adolescent females (15–17 years) with PCOS were randomly assigned to the MD group (n = 20) or the Control group (n = 20). The MD group received personalized MD plans every 15 days via a CDSS, while the Control group received general nutritional advice. Assessments were conducted at baseline and after 3 months. Results showed significantly increased MD adherence in the MD group compared to the Control group (p < 0.001). The MD group exhibited lower intakes of energy, total fat, saturated fat, and cholesterol, and higher intakes of monounsaturated fat and fiber (p < 0.05). Serum calcium and vitamin D status (p < 0.05), as well as anxiety (p < 0.05) were improved. In conclusion, tailored dietary interventions based on MD principles, delivered via a CDSS, effectively manage PCOS in adolescent females. These findings highlight the potential benefits of using technology to promote dietary adherence and improve health outcomes in this population. ClinicalTrials.gov registry: NCT06380010.