Over the past two decades, researchers have reported positive life skills outcomes for young people participating in sport-based life-skills programs. However, to date, there has been a lack of consideration in the literature regarding the quality of the programs designed and the evaluation methods adopted. Therefore, we conducted a systematic review of the life skills literature to: (a) assess the quality of sport-based life skills program design and evaluation methods; and (b) identify characteristics relating to the quality of sport-based life skills programs where authors had evidenced life skills development and transfer. Using the PRISMA guidelines, we searched six databases for relevant research papers and applied inclusion and exclusion criteria to the papers returned, of which 15 papers met the criteria. We conducted two quality assessment exercises (design and evaluation methods) and found three moderate-high quality life skills programs, 11 moderate quality programs, and one low quality program. We present the characteristics (regarding quality) of intervention designs and methods, conclude with recommendations for designing quality sport-based life skills programs, and provide guidelines for researchers to evaluate sport-based life skills programs.