Background Bariatric surgery is one of the most effective interventions for morbid obesity. Despite its benefits, unwanted consequences such as dumping syndrome (DS) have been reported following the procedure. This study aims to estimate the prevalence of DS and identify the factors associated with it in Saudi Arabia. Methodology This cross-sectional study collected data from patients who underwent bariatric surgery at King Fahad General Hospital, Jeddah, Saudi Arabia, in 2019-2020. A validated questionnaire was used to collect the data. The questionnaire included demographic items such as age and sex and items relating to DS such as nausea, vomiting, and palpitations. A modified version of the Sigstad diagnostic scoring system was used to confirm the diagnosis. Results Of the 240 investigated cases, two-thirds (67.5%) were females. The most reported symptoms were nausea (37.9%), vomiting (36.7%), desire to lie down (25.5%), restlessness (25.5%), and abdominal fullness (23.7%). Based on the modified Sigstad diagnostic scoring system, 75 (31.4%) patients met the criteria for DS. The bivariate analysis showed the prevalence was significantly higher in females (36.4%), those with university qualifications (40.3%), and those with high monthly income (62.5%) (p<0.05). Also, dietary behaviors in terms of frequency, size of meals, and drinking liquids with meals were significantly associated with the prevalence of DS, where the lowest prevalence was recorded among those who ate more than one small meal (10.9%), while the highest prevalence was found in those who ate more than one large meal (81.8%); also, the prevalence was significantly higher in patients who drank liquids with meals (40.8%) than those who drank liquids between meals (26.8%) (p<0.05). Conclusion In this single institutional study, we report a 31.4% prevalence of DS among our cohort. The predictors of the syndrome include gender, education level, monthly income, eating more than one large meal per day, and drinking liquids with meals. In the future, these predictors will be explained to patients before and after bariatric surgery to reduce the prevalence of such inconvenient syndromes., Competing Interests: The authors have declared that no competing interests exist., (Copyright © 2022, Alsulami et al.)