The present study examined self-reported sleep across the menstrual cycle and the relationship between dysmenorrhea and sleep. The participants were 89 female college students. Analyses revealed variability in two measures of nighttime wakefulness across the menstrual cycle, as well as variability in global measures of sleep and a measure of nighttime wakefulness as a function of dysmenorrhea severity. Additionally, measures of dysmenorrhea were directly correlated with scores on the Insomnia Severity Index and the Pittsburgh Sleep Quality Index. Further, participants having insomnia rated their dysmenorrhea as being more severe and causing more interference with daily activities than participants not having insomnia. The results are discussed with implications for future research.