Objectives To compare outcomes of monochorionic diamniotic (MCDA) twin pregnancies by in vitro fertilization (IVF) vs. spontaneously conceived counterparts. Methods Retrospective comparison. Data about MCDA twin pregnancies, conceived spontaneously or by IVF, attending the Twin Pregnancy Care Unit of Sant’Anna Hospital in Turin (Italy) between January 1st 2010 and March 31st 2022, were collected retrospectively. Obstetric, fetal, and neonatal outcomes of MCDA twin pregnancies by IVF were compared to those of spontaneously conceived counterparts. Data were described by univariate and multivariate analysis. Results 541 MCDA twin pregnancies were included in the study, among which 45 conceived by IVF and 496 spontaneously conceived. Women with IVF twins were older than those who conceived spontaneously (36.7 ± 5.7 vs. 32.1 ± 5.2 years; p Conclusions Our results suggest that MCDA twin pregnancies following IVF are not at increased risk of adverse outcomes compared to spontaneous MCDA twin pregnancies.