Multiple pregnancies have devastating consequences on the herd economy of dairy cattle. This observational study examines incidence patterns based on data from the ultrasonographic examination of 1130 multiple pregnancies in cows in their third lactation or more carrying twins (98.8%), triplets (1.1%), or quadruplets (0.08%), and 3160 of their peers carrying singletons. Cows became pregnant following a spontaneous estrus with no previous hormone treatments. Irrespective of a significant decrease (p < 0.0001) in the conception rate (28-34 days post-insemination) during the warm period of the year, the multiple pregnancy rate was similar for both warm (26.5%) and cool (26.3%) periods. The incidence of unilateral multiple pregnancies (all embryos in the same uterine horn) was higher than that of bilateral pregnancies (at least one embryo in each uterine horn): 54.4% versus 45.6% (p < 0.0001). This difference rose to 17% during the warm season (p = 0.03). Pregnancy was monitored in unilateral multiple pregnancies until abortion or parturition (n = 615). In the warm period, the parturition rate was 43% compared to 61% recorded in the cool period (p < 0.0001). Thus, a warm climate is the main factor compromising the fate of multiple pregnancies. Some clinical suggestions are provided.