Objective: To compare adverse perinatal outcomes between scheduled and unscheduled repeat cesarean deliveries performed prior to 39 weeks' gestation. Materials and Methods: The authors performed a single-center, retrospective cohort study comparing scheduled, and unscheduled repeat cesarean deliveries. Outcomes compared included (1) adverse operative injuries, (2) excessive blood loss, defined as drop in Hg greater than then 97% (3.6 g), or need for blood transfusion, and (3) adverse neonatal outcome (low 5-minute Apgar, or NICU admission). The presence of any adverse event, and the number of adverse events per 100 deliveries were compared between scheduled and unscheduled cases. Results: A total of 724 repeat cesarean deliveries were reviewed, of which 48.9% (n = 354) were unscheduled. There were significantly more adverse outcomes in the unscheduled cesarean cohort (32 per 100 deliveries), compared to the scheduled cesarean cohort (13 per 100 deliveries) (p < 0.001). When compared with those undergoing scheduled cesarean deliveries, women with unscheduled repeat cesarean deliveries were noted to have increased adverse outcomes (OR 3.11, 95% CI 2.04-4.74). Conclusion: Almost half (48.9%) of patients with previous cesarean deliveries deliver for either maternal or fetal indication prior to 39 weeks of gestation, and carry greater risk for adverse perinatal outcome.