This review examines the preferred route of delivery in accordance with neonatal and maternal outcome of three high risk pregnancy conditions: multiple pregnancy; delivery after cesarean section; and delivery of infants with macrosomia to mothers with gestational diabetes mellitus. The most common feature of all these conditions is the lack of information, based on large prospective controlled studies, available to the treating physician for choosing the delivery route of choice and for minimizing morbidity and mortality of both infant and mother.