Background <p>Cesarean section (CS) rates remain high globally. Previous cesarean section (PCS) is a key determinant of subsequent delivery patterns, but systematic evaluations of perioperative processes and short-term postpartum outcomes are limited.</p> Objective <p>This study aimed to quantify the association between a history of PCS and cesarean delivery at the index birth, and to describe repeat cesarean delivery specifically within the PCS group. We also explored whether the number of prior cesarean sections was associated with delivery mode and selected short-term maternal outcomes.</p> Methods <p>This single-center retrospective cohort study enrolled 892 women with singleton term deliveries between January 1, 2022, and June 30, 2025. Participants were divided into PCS and non-PCS groups. The primary outcome was cesarean delivery at the index birth in the overall cohort. In the PCS group, this outcome represented repeat cesarean delivery; in the non-PCS group, it represented primary cesarean delivery. Repeat cesarean delivery was therefore reported as a PCS-specific descriptive outcome rather than as the common outcome definition for both groups. Secondary outcomes included trial of labor after cesarean (TOLAC), VBAC success, operative time, peripartum hemoglobin decline, severe maternal adverse events, and 30-day postpartum healthcare re-contact. Weighted generalized linear models were used to estimate risk ratios (RRs) and 95% confidence intervals (CIs), and dose-stratified and sensitivity analyses were performed.</p> Results <p>A history of PCS was associated with a higher likelihood of cesarean delivery at the index birth (weighted RR 4.28, 95% CI 3.61–5.07). Among women with PCS, cesarean delivery at the index birth corresponded to repeat cesarean delivery. Dose-stratified analysis showed weighted RRs of 3.72 (95% CI 3.01–4.60) for one PCS and 5.41 (95% CI 3.89–7.52) for two or more PCS, with a significant trend. Among women with PCS, 98/221 (44.3%) attempted TOLAC, and 56/98 (57.1%) achieved VBAC. Thirty-day postpartum healthcare re-contact was higher in the PCS group (12.2% vs. 6.3%; weighted RR 1.73, 95% CI 1.15–2.60). Sensitivity analyses, including multiple imputation and propensity score matching, confirmed these findings.</p> Conclusion <p>In this selected single-center cohort of term singleton deliveries, a history of PCS was associated with a higher likelihood of cesarean delivery at the index birth. Because cesarean delivery in the PCS group represents repeat cesarean delivery whereas cesarean delivery in the non-PCS group represents primary cesarean delivery, the findings should be interpreted as associations with delivery mode rather than as evidence of a causal effect. These findings highlight the association between PCS and cesarean delivery at the index birth, while repeat cesarean delivery should be interpreted specifically within the PCS group, emphasizing the need for careful antenatal planning.</p>