The purpose of this article is to describe the evolution and influence of Masters Player-Coaches (MPCs) in the Asociación de Futbolistas Adultos Mayores del Tolima (in English: Masters Athletes’ Football Association of Tolima in Colombia, South America), a football league for men aged 60–70+ years. Historical forces shape a cultural backdrop that pervades football (soccer) and coaching and provides an understanding of how MPCs perceive themselves. After exploring the evolution and influence of the league, the authors uncover a peer-coaching approach in Asociación de Futbolistas Adultos Mayores del Tolima, described by the MPCs as Compañero Orientador. The authors link the importance of formally acknowledging the MPCs with their influence in fighting ageism, community building, and promoting lifelong sport. Further, MPCs provide high-quality Masters sport experiences, and their recognition supports a formal sporting structure in applying for local government grants to support the growing Masters context in Colombia.