The course and outcome of twin pregnancies differ from that of singleton pregnancies by the average duration of the pregnancy and the prevalence of some complications during pregnancies, the route of delivery and associated complications, as well as by prevalence of poor neonatal outcomes. Besides, twin pregnancies are subject to certain specific risks, such as twin to twin transfusion syndrome. This retrospective study was conducted at the Clinical Hospital “Sveti Duh” from January 1, 2014 to December 31, 2016. The study involved 172 women who gave birth to twins and 360 women who gave birth to singletons, and were randomly selected into the control group. An analysis was performed of age and parity, incidence of diseases and specific conditions regarding the current pregnancy, procedures during pregnancy and in vitro fertilisation (IVF). Chorionicity, duration of gestation, abnormalities in fetal growth and development, perinatal death, and route of delivery were evaluated, as well as the prevalence of labour-related and postpartal complications. Neonatal outcomes and prevalence of poor neonatal outcomes were analysed as well. The comparison of twin and singleton pregnancies revealed a higher prevalence of anaemia and preeclampsia in twin pregnancies. Besides, they were more often conceived using IVF and had a significantly shorter duration of gestation, as well as a higher incidence of fetal growth retardation and perinatal death. Twins were mostly delivered by elective C-section; in case they were delivered vaginally, the incidence of episiotomy was lower. Furthermore, twins had a higher incidence of anomalous fetal presentation and lie, as well as of postpartum complications. Neonatal outcomes of twins were poorer, i.e. they had lower birth weight and birth length, and more often had an Apgar score of ≤7. The comparison of monochorionic and dichorionic pregnancies showed a greater incidence of foetal growth restriction, discordant growth, very preterm birth, and foetal hypoxia in monochorionic twins. Besides, they had lower birth weight and birth lenght, and a greater incidence of Apgar scores lower than or equal to 7.