PURPOSE: To assess the maternal and neonatal outcomes of repeated trials of labor after one previous cesarean section. MATERIALS AND METHODS: We identified and reviewed the records of all women who had had a trial of labor after cesarean section at a tertiary care center in Saudi Arabia between January 1, 2011, and December 30, 2018. The inclusion criteria were women with singleton vertex pregnancies between 24 and 42 weeks of gestation and a trial of labor after one cesarean section. The exclusion criteria were two or more previous cesarean sections, intrauterine fetal demise, breech presentation, labor induction, estimated fetal weight >4 kg, and classical or low vertical uterine incision. The pregnancy outcomes of these women were compared according to the number of trials of labor after cesarean section. RESULTS: During the study period, 1139 women met the inclusion criteria. The number of women with previous zero, one, two, or three or more trials of labor after cesarean section were 669 (58.7%), 237 (20.8%), 132 (11.6%), and 101 (8.9%), respectively. There were statistically significant trends between the four groups in age, nationality, gravidity, and parity but not in the booking status, BMI, or the hemoglobin level before a trial of labor after cesarean section. The rate of vaginal birth after cesarean section increased significantly (p<0.001) from 72.9% with zero to 93.3% with one, 93.9% with two, and 94.1% with three or more trials of labor after cesarean section. CONCLUSION: Previously successful vaginal births after cesarean delivery are associated with improved maternal and neonatal outcomes in the subsequent trials of labor after cesarean delivery.