Objectives: This study aimed to determine the prevalence and progression of diabetic retinopathy (DR) and its risk factors in patients with diabetes attending primary care centers. Methods: This study was a cross-sectional chart review that was conducted in three randomly selected primary care centers. A total of 250 patients with diabetes had three consecutive annual screenings for DR from April 2014 to April 2017. At the initial visit, the ophthalmological findings were recorded. For three successive yearly screening, the screening results were assessed to estimate the changes that occurred in the prevalence, incidence, and progression of DR in addition to the degree of association with the most predictable risk factors. Results: The initial prevalence of DR was 15.2%. In this study, the findings over three consecutive screening intervals revealed that there was a steady increase in the prevalence of DR. The findings of this study showed that there was no significant association with DR and known risk factors including sex, type of diabetes mellitus (DM), obesity, and smoking. On the other hand, the duration of DM, hemoglobin A1c level, uncontrolled diabetes, hypertension, dyslipidemia, nephropathy, insulin treatment, and age were identified as strong predictors of DR among diabetics in this study. Conclusion: DR, a serious microvascular complication of DM, is an asymptomatic disease with a slow onset and gradual progression. Primary prevention is highly recommended to control the risk factors that will delay the onset and progression of DR.