Background: The health and well-being of medical students along with their successful progression is an important concern for society. Studies across the world demonstrated a high prevalence of psychiatric morbidity and low self-esteem among medical students requires immediate attention and effective management. Aim: To compare the symptoms of depression, anxiety, and stress between the groups who have cleared all papers in the first attempt with those who have got supplementary at least in one paper during their MBBS course. Materials and Methods: Raven's Progressive Matrices Scale, Eysenck personality Questionnaire, Sinha's Anxiety Scale, Stress Reaction Check (SRC) List, and 16-Personality Factors questionnaires were used along with performance score was recorded for the objective of the study. Results: Nonparametric tests, Mann–Whitney and Wilcoxon are used and found that RSPM scores and EPQ Lie-scale scores are statistically different as the P < 0.05. Overall performance and psychological problems association are found out using Spearman's correlation test and it is found that Factor C and Tough poise under 16 PF are significantly correlated. Conclusions: The study concluded that there is a significant difference between the abstract reasoning between the two groups of students measured by RSPM. When the students are compared by taking gender as grouping variable the study concluded psychosis, lie scale value is significantly different in the two groups and the mean value is higher in the female group. It is also concluded that the stress level measured by SRC is significantly different and the mean value is higher in the female group. Furthermore, the global factors Tough poise and independence are found to be significantly different in two groups with 16 PF questionnaire.