Abstract Background: Sleep is vital for cognitive function and physical and mental well-being. Medical students are prone to reduced sleep because of extensive curriculum, competitive exam, tireless night duties, fear of failure, and countless other responsibilities. Objective: This study aims to assess the sleep quality and daytime sleepiness and to determine their associated factors related to poor sleep quality among medical students. Materials and Methods: A cross-sectional study was done among 435 students among undergraduates and postgraduates in Kakatiya Medical College, Warangal, Telangana, from January 2023 to April 2023. After obtaining informed consent, the data were collected using a self-administered questionnaire, in which sleep quality and excessive daytime sleepiness was assessed using Pittsburgh Sleep Quality Index and Epworth Daytime Sleepiness Scale, respectively. The collected data were entered into Excel sheet and exported to SPSS V 20. Data analysis was done using Chi-square test, Fisher’s exact test, and Pearson’s correlation coefficient. P < 0.05 was considered statistically significant. Results: Poor sleep quality and excessive daytime sleepiness were present in 297 (68.3%) and 105 (24.1%) students, respectively. Department of postgraduates, smoking, mobile phone use, academic performance, tea, coffee intake, and excessive daytime sleepiness had a significant association with poor sleep quality. Excessive daytime sleep and sleep quality had strong positive correlation (r = 0.823). Conclusion: Poor sleep quality was quite high among medical students. Daytime sleepiness was predominant among students with poor sleep.