A case-control study was conducted to investigate the risks of male and female oral, oropharyngeal, and hypopharyngeal cancer associated with poor oral health, mouthwash use, occupation, histories of tobacco and alcohol use, and other factors. Data were collected from all newly diagnosed patients entered into the Wisconsin Head and Neck Cancer Network over an 18-month period (N = 623). The prevalence of painful or ill-fitting dentures was significantly higher among males and females with oral cavity cancer. Relative risks for painful dentures were 5.97 (males) and 1.60 (females); for ill-fitting dentures, the relative risks were 3.15 (males) and 2.15 (females). For males, high relative risks of oropharyngeal cancer were also found to be associated with these indicators of poor dentition. Other indicators of poor oral health, including toothbrushing frequency and prevalence of broken teeth, were not associated with oral cancer. Mouthwash use was not found to carry a risk of oral cavity, oropharyngeal, or hypopharyngeal cancer. The risks of upper aerodigestive cancers with smoking and alcohol were confirmed for males, and lifetime use patterns were explored. Notable sex differences in exposure to alcohol and tobacco were found. There was little evidence that past alcohol use was related to female oral cancer.