Premature deliveries and preterm newborns are of a special significance to obstetricians. Despite great improvement in neonatal intensive care in the last two decades, prematurity is still the leading cause of neonatal mortality and morbidity. Complications associated with premature deliveries are malpresentation, prolapse of the umbilical cord, entrapment of some parts of the fetal body, as well as severe bruising or bone fractures. The injuries may also include soft tissue damage, neurological injury, or intracranial hemorrhage. Small body weight as well as the unaccomplished development of fetal vital systems make preterm newborns vulnerable to delivery trauma. The main goal of a cesarean section in extremely preterm deliveries is to reduce the number of these complications. On the other hand, premature deliveries are associated with an undeveloped lower uterine segment and other difficulties encountered during the operation, which make the procedure more complicated and difficult to perform. Therefore, the preterm delivery or delivery of a fetus with growth retardation is of great concern. In our review, we investigated previous publications regarding en caul deliveries, mostly cesarean sections. We concentrated on the neonatal outcomes and tried to establish the optimal mode and time for a premature delivery.