Objective: Although there is clear evidence that reproductive cycle events are associated with mood episodes for women with bipolar disorder, few studies have examined for relationships between these and specific clinical characteristics of the disorder. This study aimed to explore the relationship between mood symptoms associated with reproductive cycle events and features of the disorder indicative of a more severe lifetime course. Method: Totally, 158 women of at least 18 years of age participated in the study. Subjects were recruited through a specialist clinic at the Black Dog Institute, Sydney, Australia. Results: In total, 77% of women reported increases in mood symptoms during perimenstrual, postnatal or menopausal periods. These women had an earlier age of onset for depressive and hypo/manic episodes and a greater likelihood of comorbid anxiety disorders, rapid cycling and mixed mood compared to those who did not report such reproductive cycle-associated mood changes. Women who experienced postnatal episodes were also more likely to experience worse mood symptoms perimenstrually and menopausally. Conclusion: First, reproductive cycle event-related worsening of mood was associated with a more severe lifetime course of bipolar disorder, and, second, it appears that some women have a greater propensity to mood worsening at each of these reproductive cycle events. If replicated, these findings provide important information for clinicians treating women with reproductive cycle event mood changes and highlight the need for improved therapeutics for such presentations.