Background: Stillbirth is a unique challenge faced by an obstetrician, with India being the largest contributor to world's stillbirth data. Recurrent stillbirth is even more challenging for the obstetrician and family. The current study aimed at assessing the recurrence of stillbirth, causes and associated peripartum complications, to formulate a management protocol at our center. Methodology: A retrospective cohort evaluation of the data at RMRI, Bareilly, was done from December 2020 to December 2022. All the patients with a history of previous >= 1 stillbirth were included. The recurrent stillbirth rate along with the parameters affecting its causation were studied. Results: Out of a total of 2,347 pregnant females, 62 patients were identified having previous stillbirth. 17% patients had history of >=2 stillbirths. Adverse perinatal outcomes was seen in 39 subjects (62%) (OR 1.7101; 95% CI 1.0183–2.8720). Hypertensive disorders of pregnancy and fetal growth restriction (FGR) were commonest medical complications associated in equal frequency (30.4%). 16% patients had early trimester abortions. Recurrence of stillbirth was observed in 8 patients, (recurrent stillbirth rate) = 12.9%. Majority of the cases were unbooked in the present pregnancy (63%). Hypertensive disorders of pregnancy was leading causative risk factor in recurrent stillbirth cases (37.5%). Conclusions: The management of pregnancies with previous stillbirth is a unique challenge with a markedly significant incidence of occurrence of adverse perinatal outcomes and rate of recurrence of stillbirth in subsequent pregnancies. Therefore, early bookings alongside supervised help can improve perinatal outcomes in such females.