A survey of the philosophy of sport literature reveals that arguments regarding the issue of sex segregation in athletics have been advanced from time to time, but there has been little sustained discussion, no consensus, and no change in existing practice. In this paper, an effort to advance the conversation, I begin with Jane English’s seminal 1978 article as a springboard and employ existing literature on the question of sex segregation in order to raise difficulties with English’s analysis and outline the basic alternative positions that have been taken on the issue. My own contribution to the conversation is in the introduction of four distinctions – between individual and team sports, direct and indirect competition, contact and non-contact sports, and amateur and professional sports – that have not been part of the discussion about the conditions under which men and women might compete against one another. These distinctions resolve several difficulties noted by others and suggest a more nuanced conclusion about desirable changes to the structure of sporting competition.