Aim: To assess the obstetric management and neonatal outcomes in dichorionic diamniotic pregnancy where the delivery of the second twin is delayed. Case description: A case of a 28-year-old second gravida woman with a history of secondary infertility and a prior history of spontaneous abortion at 3 months of gestation pursued fertility treatment. The patient opted for in vitro fertilization embryo transfer (IVF-ET), view of oligoasthenozoospermia, transferring two grade I embryos, resulting in a dichorionic diamniotic pregnancy. At 23 weeks, preterm premature rupture of membranes (PPROM) occurred in the twin gestation, leading to complex decisions. Despite efforts, the first twin was delivered by breech and did not survive, and the second twin remained in utero with subsidence of pain. The remaining child underwent extensive medical interventions and close monitoring, and was delivered at 27 weeks. Regardless of resuscitative efforts, the second twin was demised in the neonatal intensive care unit (NICU). Conclusion: Implementing a strategic approach is vital for a successful delayed-interval delivery. Families should be informed about potential risks and complications for both the fetuses and the mother. Clinical significance: The case report emphasizes the necessity for a planned approach by highlighting the difficulties in managing delayed-interval delivery in dichorionic diamniotic twin pregnancies, particularly following problems like PPROM.