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Background: Gestational diabetes mellitus (GDM) and polycystic ovary syndrome (PCOS) are clinically distinct disorders that share important metabolic features. This Perspective proposes a non-causal intergenerational framework linking maternal PCOS-related metabolic vulnerability, susceptibility to GDM, intrauterine metabolic exposure, and later reproductive-metabolic risk in female offspring. Methods: A narrative synthesis of evidence from reproductive endocrinology, obstetrics, diabetology, developmental biology, and public health was undertaken. The strength of evidence supporting individual components of the proposed continuum was qualitatively appraised. Separately, aggregated surveillance data from Belgrade for 2015-2024 were used as a registry-based illustration of ICD-10 O24.4-coded GDM diagnoses. No formal time-series analysis, causal modeling, or forecasting was performed. Results: Evidence was strongest for the increased risk of GDM among women with PCOS and for the association between intrauterine exposure to maternal diabetes and later offspring metabolic susceptibility. Evidence linking maternal PCOS with offspring metabolic vulnerability was less definitive, while direct evidence that GDM exposure leads to clinically diagnosed PCOS in female offspring remained weak and indirect. Registry-recorded GDM rates varied across years, but this variability may reflect differences in screening, diagnostic criteria, coding, reporting completeness, and healthcare access rather than true changes in prevalence. Conclusions: The proposed GDM-PCOS continuum is a hypothesis-generating and probabilistic framework, not an established causal pathway. Its clinical value lies in connecting prevention opportunities before conception, during pregnancy, after delivery, and across the life course. Longitudinal maternal-offspring studies are required to test the proposed relationships.