In the new frontier of Masters-level sport, coaching approaches with adult athletes may prove to be quite different than with younger cohorts, and therefore demanding of novel and innovative considerations. This paper draws from emerging perspectives in research on Masters athletes (MAs) and interpretations of broader psycho-social and -pedagogical literature to advance an early roadmap guiding practical strategies for coaches and sport programmers to consider when working with MAs. We explore four content areas that may be particularly relevant for coaches working with adult sportspersons, and for future researchers seeking to confirm where coaching practices with MAs may be highly nuanced. They include: (a) tailoring the sport environment to fulfill adults’ involvement opportunities and heighten athlete commitment; (b) helping adult athletes maximize their limited time for doing sport; (c) guiding athletes to use strategies for negotiating age-related decline; and (d) fostering self-determined and engaged learners in the Masters sport context.