Introduction: Medical students are exposed to tremendous pressure, leading to stress, depression and other psychiatric disorder at increasingly higher rates. The stress and depression can affect their learning and can lead to poor quality of life. The students of different professional year may have differing reasons for being under stress and in depression. Assessing stress and depression in students of different professional years may provide better insights, and help policy makers plan appropriate interventions. Aim: To measure and compare the prevalence and severity of stress, various aspects of life affected by stress and depressive symptoms among medical students of various professional years. Materials and Methods: A cross-sectional study was conducted from February 2018 to January 2019; on 150 undergraduate medical students (50 each from 1st, 2nd and 3rd professional year) of a medical institute in Northern part of India. Mini International Neuropsychiatric Interview (MINI version 5) was used to screen for depression, Student’s Stress Dimension Questionnaire (SSDQ) was used to assess for stress prevalence and severity and to find the various aspects of life affected by stress and Hamilton Depression Rating Scale (HAM-D) was used to measure the severity of depressive symptoms. Chi-square test and one-way Analysis of Variance (ANOVA) was used to make the group comparisons. Results: Overall stress and depressive symptoms were present in 66.67% and 52% of the participants, respectively. The three groups also differed significantly in the total score of SSDQ (H=13.664, p