Background: Currently, there is little evidence to guide clinical management of pregnancies after stillbirth. Our study aims to evaluate the pregnancy outcome in pregnant women with a previous stillbirth, by applying a standardized protocol for etiologic investigations and subsequent treatment of the underlying etiology. Methods: A retrospective cohort study on a group of 100 women with history of stillbirth, occurred in single pregnancy between 2005 and 2021, was performed. All patients were followed up in their subsequent pregnancies (n = 153) in a tertiary university hospital. During the preconception period causes of stillbirth were investigated and a correction of modifiable risk factors was encouraged with a multidisciplinary approach. Data about pregnancy management, obstetric complications, gestational age at delivery, mode of delivery and neonatal outcomes were collected. Results: The analysis of previous stillbirth revealed that, by using the ReCoDe classification, the most common identifiable causes of death were fetal growth restriction (21%), placental abruption (11%) and “other placenta insufficiencies” (26.7%), whereas 15.8% of stillbirth was unexplained. Out of 153 subsequent pregnancies, 131 (85.62%) resulted in live births, 15 (9.8%) in a first trimester miscarriage, and 7 (4.57%) in second trimester miscarriage; no cases of stillbirth recurrence occurred. Obstetric complications in subsequent pregnancies included gestational diabetes (21.4%), gestational hypertensive disorders (6.1%), intrahepatic cholestasis of pregnancy (3.8%), fetal growth restriction (7.6%) and preterm birth (19.8%). The mean gestational age at delivery was 38 weeks with a mean birth weight of 2886.63 g. Conclusions: Our experience is encouraging as reflecting good outcomes in terms of live birth rate in the subsequent pregnancies, with no cases of recurrence. These results are probably due to extensive preconception investigations with a multidisciplinary approach. A preconception evaluation is, thus, essential to improve maternal and fetal outcome in case of history of stillbirth, aiming to minimize the risk of recurrence.