The inclusion of transgender athletes in sport challenges a number of long-standing cis-hetero-normative beliefs within athletics at all levels of competition. At present, there are limited resources created specifically to help inform coaches on the best ways to support transgender athletes. The following case study follows the experiences of a transgender synchronized figure skater, Mason, who was able to continue competing throughout his transition process. We conducted eight semi-structured one-on-one interviews with Mason, his teammates, his team manager, and his past and present coaches. All interviews were digitally recorded, transcribed verbatim, and subject to inductive thematic analysis which resulted in three overarching themes: (1) Relationships: managing complex relationships between coaches, athletes, and parents, (2) Planning: re-thinking current team practices to make them more inclusive of trans participation, and (3) Direct and open communication: involving trans athletes in all conversations, and actively listening to their concerns. Additionally, all participants were asked to summarize what they learned throughout this experience and gave advice to their future counterparts. Our conclusions from this case study have been succinctly packaged into ten guidelines for coaches on the inclusion of transgender athletes.