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Background/Objectives: Diabetic retinopathy (DR) is a major microvascular complication of type 1 diabetes mellitus (T1DM) and remains an important cause of preventable visual impairment. Region-specific data on the incidence and clinical predictors of DR among patients with T1DM in Saudi Arabia remain limited. This study aimed to determine the incidence of DR and identify associated demographic and systemic risk factors among patients with T1DM at a tertiary care center in Riyadh, Saudi Arabia. Methods: This retrospective cohort study included 449 patients with T1DM aged ≥9 years who were followed at King Abdulaziz Medical City, Riyadh, between 2015 and 2025. Patients were selected using a consecutive non-probability sampling technique. Data were extracted from the BESTCare 2.0A electronic medical record system and supplemented, when required, by phone-based interviews to verify selected clinical and demographic variables. Patients were classified as controls without DR or cases with DR, including non-vision-threatening DR and vision-threatening DR (VTDR), according to the International Clinical Diabetic Retinopathy Severity Scale. Multivariable logistic regression, Cox proportional hazards models, and temporal trend analysis were performed, with statistical significance set at p < 0.05. Results: The overall incidence rate of DR was 92.66 per 1000 person-years, with similar rates among males and females. In multivariable logistic regression, older age at T1DM diagnosis, longer diabetes duration, hypertension, hyperlipidemia, and albuminuria were independently associated with DR. Mean HbA1c and HbA1c variability were not independently associated with DR after adjustment. In Cox regression, older age at T1DM diagnosis was associated with higher hazards of both DR and VTDR, while hypertension was associated with VTDR. Among patients with DR, younger age at T1DM diagnosis was associated with higher odds of proliferative disease in exploratory severity analysis. Conclusions: DR was common among patients with T1DM in this tertiary-care cohort and was mainly associated with disease duration, age at diagnosis, and systemic vascular comorbidities. These findings support the importance of routine ophthalmologic screening and integrated management of systemic risk factors in patients with T1DM.