We aimed to investigate the association between blood pressure (BP) and tooth loss and the mediation effect of age. A cross-sectional study from a reference dental hospital was conducted from September 2017 to July 2020. Single measures of BP were taken via an automated sphygmomanometer device. Tooth loss was assessed through oral examination and confirmed radiographically. Severe tooth loss was defined as 10 or more teeth lost. Additional study covariates were collected via sociodemographic and medical questionnaires. A total of 10,576 patients were included. Hypertension was more prevalent in severe tooth loss patients than nonsevere tooth lost (56.1% vs. 39.3%, p < 0.001). The frequency of likely undiagnosed hypertension was 43.4%. The adjusted logistic model for sex, smoking habits and body mass index confirmed the association between continuous measures of high BP and continuous measures of tooth loss (odds ratio (OR) = 1.05, 95% CI: 1.03–1.06, p < 0.001). Age mediated 80.0% and 87.5% of the association between periodontitis with both systolic BP (p < 0.001) and diastolic BP (p < 0.001), respectively. Therefore, hypertension and tooth loss are associated, with a consistent mediation effect of age. Frequency of undiagnosed hypertension was elevated. Age, gender, active smoking, and BMI were independently associated with raised BP.