Sport is often seen as one of the last bastions of masculinity, with old and traditional clubs (notably for golf) sometimes fighting to preserve their all-male (or sometimes all-heterosexual) membership. This context may nurrish the recurring conflict between two fundamental and equally protected principles: one the one side, freedom of association, as the cornerstone of democracy, and on the other, equality and non-discrimination, as a human right designed to ensure a level playing field for all. Given the equal status, importance and constitutional protection of the two principles, there is no theoretical model designed to solve such conflict, Thus, when these two heavyweights collide in a specific situation, the judges around the world are left to carry the burden of a case-by-case appreciation and analysis, striving to find the right balance, arguably with mixed success. This article discusses the delicate balance between these principles in the world of sports and presents several of such jurisprudences from Ireland, Switzerland and the United States, whose outcomes can be qualified of mixed.