It is unclear how well self-rated oral health (SROH) reflects actual oral health status in the rural Australian population. Therefore, this study aimed to compare the clinically assessed oral health status and SROH of adults living in rural Australia. The data were from 574 participants who took part in the Crossroads II cross-sectional study. Three trained and calibrated dentists evaluated the oral health status of participants based on WHO criteria. SROH was assessed with the question ‘Overall, how would you rate the health of your teeth and gums?’, with a score ranging from excellent = 5 to poor = 1. A logistic regression analysis (LRA) was performed, allowing us to assess factors associated with SROH. The mean age of participants was 59.2 years (SD 16.3), and 55.3% were female. The key results from the LRA show poorer SROH in those with more missing teeth (OR = 1.05; 95% CI; 1.01–1.08), more decayed teeth (OR = 1.28; 95% CI: 1.11–1.46), and more significant clinical attachment loss of periodontal tissue (6mm or more) (OR = 2.63; 95% CI: 1.29–5.38). This study found an association between negative SROH and clinical indicators used to measure poor oral health status, suggesting that self-rated oral health is an indicator of oral health status. When planning dental healthcare programs, self-reported oral health should be considered a proxy measure for oral health status.