Conflicts in high-performance sports (HPS) can be tense and emotionally charged experiences for athletes, coaches, and the national and international sports federations (NSOs and IFs) involved. Such disputes raise intriguing challenges for the mediators and arbitrators charged with handling them. These disputes typically involve multiple parties, many of whom have intensely competitive personalities, and may be spread across the globe. These issues are often high-stakes and win/lose in nature. And the mediator will typically confront numerous process challenges, such as timelines that are sometimes measured in hours, jurisdictional issues, and the rigid rules and standards of various governing bodies. Mediation has proven to be a successful tool for both managing and resolving these challenging disputes, often in creative ways that repair and preserve relationships (Blackshaw 2002). The ability of good mediators to adapt to and deal with the peculiar challenges of high-performance sports disputes and to manage the unique dynamics of sports disputes is critical for mediation success in this arena. Two variables that, unsurprisingly, appear to affect mediation settlement rates significantly are the degree of difficulty of the issue, and whether it is a win/lose distributive problem such as team selection, although other factors also play a role. In this article, I have examined cases mediated through the Sport Dispute Resolution Centre of Canada (SDRCC) to identify a range of successful mediation strategies for managing the challenges of these disputes. These best practices take into consideration my own experience as well as feedback from parties, national sports organizations, and fellow mediators. Mediation is currently not widely used around the world for resolving amateur and professional sports disputes, but I believe that it will likely become increasingly useful both nationally and internationally (Mew and Richards 2005; Blackshaw 2009, 2013, 2014; Mavromati 2015). Currently, most professional sports do not widely use mediation as a formal part of their dispute resolution processes, although informal forms of dispute resolution may well be used, and parties do sometimes opt to mediate in individual cases (Bucher 2011). As a result, both amateur and professional sports represent tremendous growth areas for the use of mediation. In recognition of this opportunity, the Court of Arbitration for Sport (CAS) introduced newly amended mediation rules in 2013, which were updated further in 2016 after consultation with and input from CAS mediators. The court has also begun a push to increase the use of mediation by rejuvenating its mediation roster in the last several years and by educating the sports community about mediation (Blackshaw 2013, 2014; Mavromati 2015).