Individuals within the criminal justice system are at greater risk of substance use–related morbidity and mortality and have substantial healthcare needs. In this quasi-experimental study, we assessed utilization patterns of Massachusetts Medicaid Program (MassHealth) services and associated expenditures among drug court probationers compared to a propensity score–matched sample of traditional court probationers. Risk of reoffending, employment status, age, and living arrangement data were used to calculate propensity scores and match probationers between the two court types, producing a final sample of 271 in each court (N=542). Utilization of services and associated expenditures were analyzed using a two-part model to address the skewed distribution of the data and to control for residual differences after matching from the perspective of the payer (i.e., MassHealth). The largest categories of MassHealth spending were prescription pharmaceuticals, hospital inpatient visits, and physician visits. In the unadjusted analysis, drug court probationers exhibited greater MassHealth services utilization and expenditures than traditional court probationers. However, drug courts enrolled more females, more people at higher risk of reoffending, and more people with opioid use disorders. After controlling for differences between the two court types, the difference in MassHealth services utilization and associated expenditures did not reach statistical significance. Drug court probationers were more likely to engage with healthcare services but did not incur significantly greater expenditures than traditional court probationers after controlling for differences between the samples.