Von Willebrand disease (VWD) is the most common inherited bleeding disorder. Patients are subject to defective platelet adhesion and aggregation that characteristically presents as mucosal bleeding. Women with VWD face bleeding risks during pregnancy, delivery, and the postpartum period. The female module of the Universal Data Collection system provides an excellent resource for analyzing the characteristics of women with VWD who experienced pregnancy-related bleeding, including bleeding during miscarriage, antepartum bleeding, and postpartum hemorrhage. We hypothesized that there are characteristics that are common to women with VWD who are likely to experience pregnancy-related bleeding complications. We compared the characteristics of women with VWD who have experienced these complications to those of women with VWD who have been pregnant but have not had these complications. We then built a multivariable regression model for the purpose of identifying women with VWD who are at increased risk for pregnancy-related bleeding. We found that there are two risk factors that are associated with pregnancy-related bleeding in this group, 1) a history of anemia (OR 4.94), and 2) a history of bleeding symptoms (OR 1.36). Our results indicate that more attention needs to be paid to the manner in which providers take a bleeding history, and the instruments used. We propose that the best care is provided for these women when obstetricians and hematologists work together in a proactive approach.