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Introduction: Hypertensive disorders in pregnancy (HDP) and gestational diabetes mellitus (GDM) represent two significant maternal cardiometabolic disorders closely related to each other. This study aims to identify predictive risk factors for gestational hypertension in patients with GDM within our population. Methods: This cohort study was conducted at the Department of Obstetrics and Gynecology, Policlinico "G. Martino" of Messina from January 2012 to December 2019. It included 684 pregnant women diagnosed with GDM by Oral Glucose Tolerance Test (OGTT) according to Italian guidelines. A detailed medical history was taken for each patient to identify potential predictive risk factors for HDP. Patients with pre-existing hypertension or diabetes were excluded. Results: Among 684 women with GDM, 69 (10.1%) developed hypertensive disorders of pregnancy (HDP). Women with HDP had a significantly higher pregestational BMI (30.1 ± 7.7 vs. 26.5 ± 5.6 kg/m², p = 0.001) and a higher prevalence of obesity (51% vs. 34%, p = 0.0001). Post-load glucose at 60 min was higher in the HDP group (178 ± 34 vs. 164 ± 32 mg/dL, p = 0.0001), with more women exceeding the diagnostic threshold (>180 mg/dL: 56% vs. 35%, p = 0.001). Multivariate analysis confirmed that pregestational obesity and higher 60-min glucose levels during OGTT were the strongest independent predictors of HDP. Conclusions: Obesity and glycemia above the cut-off after 1 h during OGTT are predictive risk factors for hypertensive disorders in patients with GDM.