Coaches contribute toward helping older adults achieve quality sport experiences, but there are few resources grounded in adult-oriented psychosocial approaches from which they can learn. The purpose of this Participatory Action Research study was to facilitate a personalized professional development program for a Colombian football (soccer) league of older adult men using an evidence-based self-assessment tool for Masters coaches. Data were collected from 23 coaches, who were also players in the league, via interviews, workshops, and observations. Data were analyzed via reflective thematic analysis that aimed to understand coaches' perceptions of how they learned through the workshops and how they implemented what they learned into their coaching. Findings indicate that personalized professional development enabled better structured leadership in the league, creating Quality Masters Sport Experiences.