Assisted reproductive technology (ART) is commonly used to achieve pregnancy and often results in dichorionic diamniotic (DCDA) twin pregnancies. However, the potential risks of ART on maternal and neonatal outcomes in these pregnancies are not well understood. The objective is to compare the maternal and neonatal outcomes in DCDA twin pregnancies between those achieved through ART and those spontaneously conceived (SC). We carried out a systematic comprehensive search of electronic databases; namely, PubMed, Embase, Scopus, and the Cochrane Library, from inception to March 2023 with a study period of recruitment between 2003 and 2023. We included all studies comparing the maternal and neonatal outcomes of DCDA twin pregnancies between those achieved by ART and those SC. We analyzed data from 18 cohort studies involving 10,485 women with DCDA twin pregnancies. The meta-analysis showed that ART-conceived pregnancies had a significantly higher risk of preeclampsia or gestational hypertension (GH), gestational diabetes mellitus (GDM), placenta previa (PP), placental abruption (PA), postpartum hemorrhage (PPH), and elective and emergency cesarean sections than SC twin pregnancies. The absolute risks of these complications remained relatively low. We also found a slightly higher risk of respiratory distress syndrome (RDS) and congenital malformations in ART-conceived infants compared to the risks in SC infants. Finally, the risk of neonatal intensive care unit (NICU) admissions was significantly higher in ART-conceived infants than in SC infants, but with high heterogeneity. We found associations between DCDA twin pregnancies conceived through ART and increased frequencies of adverse maternal outcomes. However, the absolute risks of these complications remained low, and the benefits of ART for achieving successful pregnancies may well outweigh the potential risks. Additionally, ART-conceived DCDA twin pregnancies may pose higher risks of RDS, congenital malformations and NICU, admissions than SC DCDA twin pregnancies.