Cesarean section (CS) is a life-saving procedure when performed for the right indication but carries substantial risks, specifically during subsequent pregnancies. The aim of this study was to evaluate obstetric outcomes for women 5 years after a CS performed by medical doctors and associate clinicians. This was a prospective multi-center observational study of women who had a CS at any of nine hospitals in Sierra Leone. Women and their offspring were followed up with three home visits for 5 years after surgery. Outcomes of interest included long-term complications, mode and place of delivery, and maternal and pediatric outcomes of subsequent pregnancies. Of the 1274 women included in the study, 140 (11.0%) were lost to follow-up. Within 5 years after the index CS, 27.0% of the women became pregnant and 2.5% had a second pregnancy. Women with perinatal death at the index CS had 5.25 higher odds of becoming pregnant within 1 year. Of the 259 women who delivered, 31 (12.0%) had a planned CS and 228 (88.0%) attempted a trial of labor after CS, resulting in either a successful vaginal birth (n = 138
60.5%) or an emergency CS (n = 90
39.5%). Peripartum and long-term complications did not significantly differ between those that were operated on by medical doctors and associate clinicians. Within 5 years after CS, one in four women became pregnant again and more than half had a vaginal delivery. Significant differences in place and mode of birth between wealth quintiles illustrate inequities.