As the number of mental health practitioners with interest in play therapy grows, more research is needed to add to the evidence base for play therapy training. In order to examine the impact of service learning and live supervision early in the play therapy training process, the authors assessed play therapy trainees’ (N = 12) play therapy attitudes, knowledge, and skills both before and at the conclusion of a training module. Furthermore, the authors explored the relationship between the supervisory working alliance and trainees’ perceptions of their play therapy attitudes, knowledge, and skills. At the conclusion of the service learning and live supervision training module, participants demonstrated significant gains in measures of self-competence related to play therapy, and self-perceived skill competence correlated positively with the supervisory working alliance. The authors conclude that service learning can effectively be incorporated into the early phases of play therapy training when live supervision is utilized to safeguard the integrity of services.