Background: Diabetes mellitus, a prevalent metabolic disease globally, causes various complications, including microvascular issues like Diabetic Retinopathy (DR) and macrovascular complications. DR, characterized by retinal microvascular alterations, is a leading cause of vision loss. Diabetic Foot Ulcer (DFU) is a severe complication, often leading to amputation, with studies suggesting a link between DR and DFU. This study aims to assess the severity of DR concerning different grades of DFU. Objective: To evaluate the association between the severity of Diabetic Retinopathy and various grades of Diabetic Foot Ulcer. Methodology: A cross-sectional study was conducted from February 2021 to August 2022, involving 100 patients clinically diagnosed with type 2 Diabetes Mellitus and DFU. Data on socio-demographics, medical history, and DR severity were collected. Statistical analysis was performed using SPSS, with a significance level of 5%. Result: Participants (n=200) were primarily aged 51-60 (39%), with 62% males. About 42% had diabetes for 1-5 years, and 73% reported DFU duration of <1 month. In DR grading, 26% had Moderate NPDR, 15% had severe NPDR, 4% had very severe NPDR, and 21% had no NPDR. A significant association was found between DR severity and DFU grades (p<0.05). Discussion: Comparisons with existing studies revealed variations in diabetes duration and DR severity. The study confirmed the association between DFU and DR, consistent with previous findings. Conclusion: The study emphasizes the need for enhanced screening protocols to detect and manage DR and DFU promptly. The severity of DR increases with DFU stages, suggesting DFU's potential to predict advanced DR stages. As diabetes prevalence rises, addressing these complications is crucial for the working population's well-being. A systematic healthcare approach is essential for early detection and management.