Bullying remains a pervasive problem in schools across the nation. Various detrimental social, psychological, emotional, and academic effects can result from involvement in bullying regardless of whether a student is the perpetrator, victim, witness, or a combination of the three. Recent literature has made significant connections between a school’s overall climate and bullying behaviors, suggesting the need for school-wide interventions to combat the problem. As a part of school climate, unstructured areas such as the playground, have been targeted as a critical area in need of support. Researchers attribute poor safety on the playground to lack of adequate and trained supervision. Fortunately, Systematic Supervision is a training program based in empirically supported principles that shows likelihood for success to improve climate and reduce bullying behaviors on the playground and the school as a whole (Smith, & Sprague, 2011). Yet, this program has not been thoroughly evaluated in peer reviewed journals. The purpose of this study was to evaluate the effectiveness of Systematic Supervision for improving playground safety, reducing bullying behavior, and enhancing school climate. Behavioral observations and student and teacher school climate surveys collected from 35 schools over two years were assessed. Comparisons were made between schools that received the intervention with those that were wait-listed controls. Results of the study suggest that Systematic Supervision is an effective means of training playground monitors to use active supervision behaviors. Unfortunately, no significant connections could be made with regard to the implementation of Systematic Supervision and subsequent changes in student or teacher perceptions of safety, in perceptions of school climate, or in bulling behaviors. A discussion of the results and their implications is included in detail.