Multiple pregnancy is a condition where more than one fetus occupy the same intrauterine cavity. By means of its rarity in spontaneous pregnancies, it indicates that that by nature the human female uterus is programmed to carry one fetus at a time. The incidence of multiple pregnancy is on the increase because of fertility treatment especially assisted reproductive technology. Unfortunately, multiple pregnancy is associated with several complications from conception until the postpartum period. Maternal uterine anomalies also pose special challenges if associated with multiple pregnancy from diagnosis until management. Miscarriages are higher and some of them are not noticed if the pregnancy continues with one fetus. There are complications related to uterine space like preterm labour which is the commonest. Rupture of membranes with or without preterm labour is also common. Monochorionic multiple pregnancies poses specific challenges in respect to abnormalities during organogenesis from embryonal to vascular malformations. Fetus growth discordance and single twin demise are uncommon but challenging.