Current early diagnosis, surveillance and intervention options make it hard to determine the natural course of twin pregnancies, especially regarding spontaneous preterm delivery and perinatal mortality. We studied the natural course in monochorionic (MC) and dichorionic (DC) twin pregnancies in a historical cohort. Twin pregnancies were studied in a unique database of 651 twin pairs born in the period 1907 to 1938. We examined the effect of chorionicity on gestational age, birthweight, peri-natal mortality, intertwin birthweight differences, the incidence of preeclampsia and maternal mortality. Perinatal mortality was 27.7% for MC and 15.8% for DC twins (p < .001). Gestational age and birthweight were stronger predictors of perinatal mortality than chorionicity. Perinatal outcome was poorer for the second twin, especially in DC twins. Delivery before 37 weeks of gestation occurred more often in MC twin pregnancies (48.8% compared to 33.3% in DC twin pregnancies). DC twins were on average 288 g (95% confidence interval 201–376) heavier than MC twins. Severe birthweight discordancy occurred equally in MC and DC twins (18.1%). However, if present, mortality was only increased in MC twins. The birthweight of girls was not affected by the presence of a male co-twin. In this historical cohort MC twin pregnancies had a higher perinatal mortality, caused by a high incidence of low birthweight mainly due to preterm delivery. Mortality did not differ in deliveries after 31 weeks of gestation, which is in contrast to recent data. Apparently, modern obstetrics is more effective in reducing mortality in DC twins.