Hypertension and periodontal disease are common conditions among postmenopausal women. Periodontal disease has been found associated with hypertension in previous studies, but data in postmenopausal women is limited. We assessed the cross-sectional associations of clinically measured periodontal disease with prevalent hypertension and measured systolic blood pressure (SBP) among 1341 postmenopausal women enrolled in the Buffalo Osteoporosis and Periodontal Disease (OsteoPerio) study, an ancillary study of the Women's Health Initiative-Observational Study. Clinical attachment level (CAL) and number of teeth missing were positively associated with SBP among those not taking antihypertensive medication in crude and multivariable adjusted linear regression models (both P < 0.05). Alveolar crestal height (ACH) and gingival bleeding on probing were associated with higher SBP in crude but not multivariable adjusted models. Neither probing pocket depth (PPD) nor severity categories of periodontitis were associated with SBP. Number of teeth missing was significantly associated with prevalent hypertension in crude and multivariable adjusted models (OR = 1.14, per 5 teeth; P = 0.04). ACH was associated with prevalent hypertension in crude but not adjusted models. CAL, PPD, gingival bleeding, and severity of periodontitis were not significantly associated with prevalent hypertension. These results suggest that measures of oral health including CAL and number of teeth missing are associated with blood pressure in postmenopausal women. Prospective studies are needed to further investigate these associations and the potential underlying mechanisms for these relationships. © 2018 American Academy of Periodontology.