The authors present results from a randomized controlled trial of a school-based intervention that provided services to youth with prior police contact. The youths’ prior police involvement ranged from police contact without an arrest to being placed on probation. The intervention used a wraparound-style approach and a school-based, multisystem team to deliver services to youth. The study took place over 3 years and used a rolling enrollment strategy. Youth (N = 869) were assigned to either an intervention condition or a business-as-usual control condition using a block randomization strategy. Outcomes came from school records and state Department of Juvenile Justice records. Cox regression analyses were used to predict time to first post-enrollment school suspension and juvenile justice system contact from intervention condition. Intervention condition did not predict time to first post-enrollment suspension or juvenile justice system contact. It also did not predict alternative specifications of these outcomes (i.e., in- versus out-of-school suspension and misdemeanor versus felony contact). Subgroup analyses revealed similar null results for youth with varying types of prior police contact, though statistical power was limited. The lack of beneficial intervention effects may stem from challenges in implementing this approach to improving behavior among students with prior police contact. Multisystem school-based interventions for these youth require the cooperation and coordination of multiple staff and stakeholders. Efforts to improve both service implementation and the augmentation of services that youth already receive from schools and the justice system may improve youth outcomes.