The purpose of this study was to explore the efficacy of using loyalty programs on sport fans’ relationship quality and fan engagement toward sport organizations. This study also sought to explore which relationship quality and fan engagement factors potentially differed as a result of using loyalty programs. Since there are two major defined sport levels, differences were explored across niche and mainstream sport organizations. Using relationship marketing as the theoretical framework, participants (n = 678) were administered a 55-item instrument that included revised relationship quality and fan engagement scales. Quantitative data were used to run confirmatory factor analyses, analyses of covariance, and multivariate analyses of covariance. Results first showed that significant differences existed between mainstream sport fans that have access to a loyalty program and mainstream sport fans that do not have access to a loyalty program. Mainstream sport fans that have access to a loyalty program had higher identification and reciprocity. Mainstream sport fans that do not have access to a loyalty program were found to have higher overall fan engagement, commitment, intimacy, and performance tolerance. Results also showed differences between niche sport fans that have access to a loyalty program and mainstream sport fans that have access to a loyalty program. Mainstream sport fans that have access to a loyalty program were divided into two groups (simple or complex) based on the design of the loyalty programs. Niche sport fans that have access to a loyalty program were found to have higher overall relationship quality, trust, intimacy, management cooperation, and performance tolerance. The findings provide an introduction in to the possibility that loyalty programs could be effective for increasing relationship quality for both niche and mainstream sport organizations. Moreover, for niche sport organizations that have access to fewer resources, it is encouraging that the use of a loyalty program appears to have the capabilities to build stronger relationships and engagement. These results provide several implications for sport organizations and sport marketers and serve as a foundation for which future research on loyalty programs can build.