Objective: This study examines whether children delivered by repeat cesarean section experience higher incidences of otitis media, respiratory infections, and allergic diseases than children delivered by vaginal birth after cesarean section (VBAC) in the Military Health System. Study Design: This is a retrospective cohort study from the Military Health System Data Repository of women who underwent repeat cesarean section or VBAC between 2006 and 2012 and their offspring through 2014. Results: About 11,659 infants with 2 years of follow-up were identified. Infants delivered by VBAC had lower odds of developing respiratory illness (P <. 000), otitis media (P <. 001), and allergies (P =. 022) compared with infants born by repeat cesarean section. There were no differences in the development of food allergies. Conclusion: Emerging data regarding early childhood health are additional factors that can influence the mother's decision on mode of birth after a primary cesarean section.