Background: Dysmenorrhea (painful menstrual cramps) is one of the most common gynecological complaints in women and girls. Dysmenorrhea may be a condition itself or a result of another medical condition, including endometriosis and chronic pelvic pain. Research examining the relationship between menstrual pain ratings and catastrophizing has produced mixed results. Objective: To review and meta-analyze the relationship between catastrophizing and pain ratings of chronic cyclical pelvic pain. Design: Cross-sectional, longitudinal, and intervention studies that reported the relationship between menstrual/pelvic pain and catastrophizing were included. Study populations had to include healthy menstruating persons or persons with a condition associated with cyclical pelvic pain including primary dysmenorrhea, endometriosis, and/or chronic pelvic pain. Data sources and methods: A systematic search of articles published since 2012 on PubMed, PsychInfo, CINHAL, and Medline was conducted in January and rerun in November of 2022. Search terms included cyclical pelvic pain, dysmenorrhea, endometriosis, pelvic pain, and catastrophizing. Data extraction was completed independently by two extractors and cross-checked for errors. A random-effects meta-regression was used to synthesize the data using restricted maximum likelihood. Results: Twenty-five studies examining 4,540 participants were included. A random effects model found a meta-correlation between catastrophizing and pain of r = .31 (95% confidence interval: .23–.40) p < .001. Heterogeneity was large and significant ( I2 = 84.5%, Q(24) = 155.16, p < .001). Studies that measured general pelvic pain rather than cyclical pelvic pain specifically and those that used multi-item rather than single-item measures of pain had significantly higher correlations. Age and depression did not moderate the relationship between catastrophizing and pain. Conclusion: A systematic review and meta-analysis found that catastrophizing had a small but significant positive association with pain ratings. Patients experiencing cyclical pelvic pain may benefit from interventions targeting the psychological management of pain. Registration: This meta-analysis was registered in PROSPERO on 14 January 2022. Registration number: CRD42022295328.