Background Diabetic retinopathy (DR) is one of the major complications of diabetes mellitus (DM) and the leading cause of blindness among adults. However, adherence to diabetic retinopathy screening (DRS) significantly reduces blindness. A substantial proportion of diabetics have suboptimal compliance to DRS, which inversely affects their outcomes. Therefore, the aim of this study is to determine the level of adherence to DRS and to explore the factors possibly associated with poor adherence to regular screening among diabetics in Riyadh, Saudi Arabia. Method A cross-sectional study was conducted that encompassed 404 adult diabetic patients attending outpatient clinics in four hospitals in Riyadh. A validated, self-administered questionnaire was used for data collection that included five main sections: sociodemographic data, diabetic profile, assessment of knowledge about DR, attitude toward DRS, and barriers to DRS. Data were analyzed by SPSS, version 23 (IBM Corp., Armonk, NY); qualitative variables were described as percentages, and quantitative variables were described as means ± standard deviation (SD). We used the chi-square test to measure the associations between qualitative variables and binary logistic regression analysis to predict the independent barriers to DRS. Result The average age of the participants was 54 years, and 69.1% were females. The average duration of diabetes was 12.3 years. Type 2 DM was the most prevalent form of DM (63.6%). DR was reported by 20% of participants. Poor knowledge about DRS was prevalent in 51%. More than one-fifth were never screened for DR. About one-third of participants agreed that cost was an important contributing barrier. Adequate knowledge, increased duration of diabetes, and presence of neurological complications increased independent adherence to screening. Conclusion One-fifth of participants reported having DR. Half the participants had poor knowledge about DR, which formed a major barrier against regular screening. However, most participants had positive attitudes about DR screening. Therefore, intervention strategies to increase patients' awareness of DR might be the cornerstone of ensuring proper adherence to DRS.