Background Preterm birth before 37 weeks of gestation is a global public health challenge, particularly in India, where the prevalence varies regionally. Understanding risk factors, such as maternal age and complications like hypertensive disorders, is vital. India's diverse healthcare landscape and regional disparities further complicate this issue. Preterm infants face increased mortality and morbidity risks like respiratory distress and intraventricular hemorrhage. This study in a tertiary care hospital aimed to analyze risk factors, assess perinatal outcomes, and contribute to the understanding of preterm birth in this complex context, providing valuable insights for maternal and child health strategies. Methods This retrospective cohort study was conducted at the Venkateshwara Institute of Medical Science, Rajabpur, over one year, extracting data from electronic health records. The study aimed to analyze risk factors associated with preterm delivery and assess perinatal outcomes. The study included diverse pregnancies, both singleton and multiple gestations, and employed sample size calculations to ensure statistical validity. Trained medical personnel collected extensive data on maternal characteristics, obstetric history, antenatal care, perinatal outcomes, and mode of delivery. Statistical analysis, utilizing SPSS (IBM, Chicago, USA), involved descriptive statistics, comparative analysis, chi-square tests, t-tests, Mann-Whitney U tests, and multivariate logistic regression models. Findings with a p-value <0.05 were considered significant. Results The study included 2042 deliveries, with a preterm birth prevalence of 14.2%. Multiparous women had higher preterm birth rates than primigravida (72.92% vs. 27.08%). Maternal age, history of preterm delivery, hypertensive disorders, inadequate antenatal care compliance, previous cesarean section, multiple gestations, antepartum hemorrhage (APH), polyhydramnios, oligohydramnios, and premature rupture of membranes (PROM) were significantly associated with preterm birth. Apgar scores at one minute and five minutes, neonatal complications, and mortality rates were notably worse among preterm births. Vaginal delivery rates were significantly lower in the preterm group (36.3%) compared to full-term deliveries (48.8%), with a higher rate of emergency cesarean sections (19.7% vs. 10.8%). Conclusion This study provides valuable insights into the risk factors and perinatal outcomes of preterm delivery at a tertiary care hospital, with precise values illustrating the extent of associations. The findings such as history of preterm delivery, hypertensive disorders, and inadequate antenatal care compliance as the most commonly associated conditions with preterm birthand management of such associated conditions may help reduce the rate of premature birth.