Background: Guideline-based breast and cervical cancer screenings are fundamental components of high-quality preventive women’s health care services. Accurate measurement of screening rates is vital to ensure all women are adequately screened. Our systematic review and meta-analysis aims to provide an updated synthesis of the evidence on the accuracy of self-reported measures of cervical and breast cancer screening compared to medical records. Methods: To identify studies, we searched MEDLINE®, Cochrane Database of Systematic Reviews, and other sources up to July 2019. Two reviewers sequentially selected studies, abstracted data, and assessed internal validity and strength of the evidence. Adjusted summary numbers for sensitivity and specificity were calculated using a bivariate random-effects meta-analysis. Results: Unscreened women tended to over-report screening among 39 included studies examining the accuracy of self-report for cervical and/or breast cancer screening. The specificity of self-report was 48% (95% CI 41 to 56) for cervical cancer screening and 61% (95% CI 53 to 69) for breast cancer screening while the sensitivity of self-report was much higher at 96% (95% CI 94 to 97) for cervical cancer screening and 96% (95% CI 95 to 98). We have moderate confidence in these findings, as they come from a large number of studies directly assessing the accuracy of self-report compared to medical records and are consistent with findings from a previous meta-analysis. Conclusions: Unscreened women tend to over-report cervical and breast cancer screening, while screened women more accurately report their screening. Future research should focus on assessing the impact of over-reporting on clinical and system-level outcomes.