Advances in antiretroviral therapy (ART) have dramatically reduced the risk of mother-to-child transmission (MTCT) of HIV, leading to substantial changes in obstetric management. However, data describing the implementation of updated recommendations in routine clinical practice, particularly regarding mode of birth after a previous cesarean section (CS) and delayed cord clamping (DCC), remain limited. We aimed to evaluate temporal changes in intrapartum and postpartum management among women living with HIV (WLWH) over a 17-year period at a tertiary referral center. We conducted a retrospective cohort study including all WLWH who delivered at a university hospital between January 2009 and December 2025. Pregnancies were categorized into three periods according to major changes in national recommendations on mode of birth: 2009–2013, 2014–2018, and 2019–2025. Maternal HIV characteristics, ART, obstetric management, and delivery and neonatal outcomes were compared among study periods. Sixty-three women had 83 pregnancies during the study period. The proportion of women receiving ART at conception increased significantly over time (p < 0.001), paralleled by a shift toward contemporary antiretroviral regimens. At delivery, only three women had a viral load ≥50 copies/mL, all during the earliest study period. Planned pre-labor CS declined significantly (p < 0.001), whereas vaginal delivery increased, reaching 51.8% in 2019–2025, without any case of vertical HIV transmission. Among women with a previous CS managed after 2014, the acceptance rate of a trial of labor after CS (TOLAC) was 53.3%. All women declining TOLAC cited fear of HIV transmission despite viral suppression. DCC was performed in 89.4% of newborns, with no adverse neonatal outcomes attributable to the procedure. Contemporary multidisciplinary management of WLWH enables high rates of viral suppression, increasing use of vaginal birth, and implementation of DCC with no case of vertical transmission observed. Given the sample size and observational design, these findings are reassuring but not conclusive. Nevertheless, previous HIV-related cesarean delivery continues to influence women’s decisions regarding mode of birth in subsequent pregnancies, highlighting the need for individualized counseling to facilitate evidence-based shared decision-making.