Background/Objectives: Osteoporosis and periodontal disease (PD) are associated with significant morbidity and mortality especially among post-menopausal women. The attributable causes of mortality include bone fragility, hip fractures, surgical risks, complications associated with immobility/disability, and mental health issues. This cross-sectional study aims to investigate the association between oral health and bone diseases along with the factors that predict this association. Methods: This study included post-menopausal women undergoing routine bone density evaluation. Following informed consent, case histories were collected using an investigator-administered questionnaire. The oral cavity was inspected for the health of the oral structures and periodontium. Bone density data, interpreted by a radiologist, were also collected. Data were analyzed using chi-square and logistic regression tests with the significance level set at 5%. Results: Among 100 eligible participants, mean age and body mass index (BMI) were 68.17 ± 8.33 years and 29.59 ± 6.13 kg/m2, respectively. A total of 23 participants (23.0%) had T2DM, 29 (29.0%) had < 20 natural teeth, and 17 (17.0%) had normal bone mineral density. Except for age (aOR 1.171, p < 0.001), BMI (aOR 0.763, p < 0.001), and past osteoporotic fractures (aOR 21.273, p = 0.021), all other factors were insignificant predictors of bone loss. Conclusions: Although the unadjusted results suggest a relationship between oral health indicators and bone loss, these relationships were not present when other factors were included in an adjusted model. Our findings suggest PD by itself may not be a risk factor for bone loss but that the two conditions may have similar risk factors.