Few studies have investigated the relation between oral health-related quality of life (HRQL) and key demographic, socioeconomic, and oral health decrements. Methods: Data were taken from 873 participants from the Florida Dental Care Study. Chronic oral disadvantage was defined from incident oral disadvantage, a measure of oral HRQL, reported for a minimum of two consecutive 6-month intervals. Patterns of chronic oral disadvantage over the 24-month period were described. Associations between the dependent variable, chronic oral disadvantage, and demographic variables, socioeconomic variables, oral health decrements, and dental services were evaluated. Results: During 24 months of follow-up, 30% of subjects reported chronic oral disadvantage. Chronic oral disadvantage was significantly associated with approach to dental care, area of residence, situation if faced with an unexpected $500 dental bill, teeth that are stained or look bad, cavities, sore or infected gums, loose tooth or cap, toothache or abscess, dental sensitivity, and chewing difficulty. A recent dental visit was associated with reduced progression to chronic oral disadvantage. Conclusion: A large proportion of subjects avoided certain daily activities due to oral health decrements for longer than 6 months. Recent dental visits were significantly associated with limitation of long-term progression of oral disadvantage.