Background: Psychiatric illness is a well-established risk factor for criminal justice system involvement, but less is known about the relationships between specific psychiatric illnesses and reoffending. Research typically examines reoffending as a single discrete event. We examined the relationship between different psychiatric disorders and types of reoffending while accounting for multiple reoffending events over time. Methods: Data were drawn from a population cohort of 83,039 individuals born in Queensland, Australia, in 1983 and 1984 and followed to age 29–31 years. Psychiatric diagnoses were drawn from inpatient health records and offending information was drawn from court records. Descriptive and recurrent event survival analyses were conducted to examine the association between psychiatric disorders and reoffending. Results: The cohort included 26,651 individuals with at least one proven offence, with 3,580 (13.4%) of these individuals also having a psychiatric disorder. Individuals with any psychiatric disorder were more likely to reoffend compared to those without a disorder (73.1% vs. 56.0%). Associations between psychiatric disorders and reoffending varied across age. Individuals with a psychiatric disorder only started to accumulate more reoffending events from ~ 27 years, which accelerated up to age 31 years. There were both specificity and common effects in the associations between different psychiatric disorders and types of reoffending. Conclusions: Findings demonstrate the complexity and temporal dependency of the relationship between psychiatric illness and reoffending. These results reveal the heterogeneity present among individuals who experience psychiatric illness and contact with the justice system, with implications for intervention delivery, particularly for those with substance use disorders.