Dental caries is a chronic and cumulative disease but little has been reported on the continuity of the disease and its treatment through life. Group-based multi-trajectory modeling was used to identify developmental trajectories of untreated carious tooth surfaces (DS), restored tooth surfaces (FS), and teeth extracted due to caries (MT) from ages 9 to 45 years in a New Zealand longitudinal birth cohort, the Dunedin Multidisciplinary Health and Development Study (n = 975). Associations between early-life risk factors and trajectory group membership were examined by specifying the probability of group membership according to a multinomial logit model. Six trajectory groups were identified and labeled: “low caries rate”; “moderate caries rate, maintained”; “moderate caries rate, unmaintained”; “high caries rate, restored”; “high caries rate, tooth loss”; and “high caries rate, untreated caries”. The two moderate-caries-rate groups differed in count of FS. The three high-caries-rate groups differed in the relative proportion of accumulated DS, FS, and MT. Early childhood risk factors associated with less favorable trajectories included higher dmfs scores at age 5, lack of exposure to community water fluoridation during the first 5 years of life, lower childhood IQ, and low childhood socioeconomic status. Parent self-ratings of their own or their child’s oral health as “poor” were associated with less favorable caries experience trajectories. Children who had clinical signs of dental caries together with a parent rating of child’s oral health as poor were more likely to follow a less favorable caries trajectory. Higher deciduous dentition caries experience at age 5 years was associated with less favorable caries trajectories, as were children whose parents gave “poor” ratings of their own or their child’s oral health. These findings highlight the considerable intergenerational continuity in dental caries experience from early childhood to midlife. Subjective measures of child oral health are informative and might aid as predictors of adult caries experience in cases where childhood dental clinical data were not available.