Background Medical students' syndrome (MSS) is a set of psychosomatic symptoms that affect students due to their medical background knowledge. Objectives This study aims to measure the prevalence and assess the knowledge about MSS among medical students at the University of Sharjah. It also aims to compare the attributed characteristics of MSS between different years of study. Methods A self-administered 24-item questionnaire was distributed to 503 students enrolled in the College of Medicine at University of Sharjah using nonprobability convenience sampling during June 2021. A total of 472 responses were completed and analyzed using descriptive studies and chi-squared test. Results The prevalence of MSS in this study was found to be 70.8% ( n = 334). Clinical year students were 1.75 times more likely to have felt they had a disease they studied about (95% confidence interval: 1.05-2.90, p = 0.03). Conclusion Medical students are more likely to experience MSS as their education progresses.