Aims: To determine the prevalence and predictors of diabetic retinopathy (DR) in Saudi males and females with diabetes. Methods: This cross-sectional study enrolled 507 patients with diabetes between May and August 2018. The data extracted from patients’ records included demographic and clinical information and laboratory investigations. The retinopathy data were based on fundus photography graded into five categories: no DR, NPDR, MNPDR, SNPDR, and PDR. Results: The patients’ mean age was 47.3 years, the majority (59.3%) being female and T2DM being the most common type (52.4%). The prevalence of no DR was 51.4%; NPDR, 4.4%; MNPDR, 7.7%; SNPDR, 3.7%; and PDR, 5.1%. The duration of DM, as well as the severity of hypertension and neuropathy values rose significantly as DR progressed, underlining the pivotal role of hyperglycemia as the primary driver of diabetic complications. The odds ratio for the presence of hypertension was 1.8 (95% CI 0.9–3.5); hypertension showed the highest risk of DR. Stratification according to gender showed a significantly higher DR risk in females than males. Interestingly, nephropathy played a significant role in the DR risk in T1DM. Conclusions: Among T1DM and T2DM patients, the severity of DR is associated with risk factors including the DM duration, hyperglycemia, hypertension, and neuropathy. The impact of these factors varies with gender and diabetes type. Therefore, the severity of DR could define patients at a high risk of macro/microvascular complications and enable earlier interventions to reduce morbidity and mortality among T1DM and T2DM patients.