Background/Objectives: Although morbidity and mortality are more pronounced in extremely and very preterm infants, there is also considerable morbidity in preterm infants of more advanced gestations. Delivery via cesarean section is associated with a higher risk of perinatal complications even when performed electively. Our aim was to examine the possible contribution of prenatal and perinatal factors to the risk for respiratory morbidity in a population of late-preterm and early-term infants delivered with a high rate of elective cesarean section. Methods: In a retrospective cohort study, all late-preterm and early-term infants (34 to 38 completed weeks of gestation) that were admitted with respiratory distress to the Neonatal Intensive Care Unit of the University Hospital of Patras over a recent period of two years were included in the study. Results: In the study period, 489 infants of all gestations were admitted to the neonatal unit, of whom 221 were born between 34 and 38 + 6 gestational weeks. Ventilated infants had a significantly lower incidence of antenatal corticosteroids (41%) compared to non-ventilated infants (51%, p = 0.036) and a higher duration of parenteral nutrition [4 (1–6) days] compared to non-ventilated infants [2 (1–3) days, p < 0.001]. The incidence of late-onset sepsis was higher in the ventilated infants (26%) compared to the non-ventilated ones (8%, p < 0.001). Conclusions: Late preterm and early term infants who were invasively ventilated had less often received antenatal corticosteroids and had a higher incidence of late-onset sepsis compared to those who were not ventilated.