Abstract: The Japan Sports Agency has made efforts to unify several career support programs for Olympic athletes prior to the 2020 Tokyo Olympics. One of the programs, the Japan Olympic Committee Career Academy (JCA) was established in 2008 for Olympic athletes at their retirement. Research focusing on the service content of sport career support programs can help athletes experience a more positive transition. This study was designed to investigate the service content of the JCA program in relation to athletes’ career transition needs, including any differences of the reasons for retirement between Summer/Winter and Male/Female Olympic athletes, and to suggest the directions of how to unify the career support programs in Japan after hosting the Olympic Games using sport career transition models. Semi-structured interviews were conducted and analyzed the JCA director who started and managed the program since its inception, and a total of 15 conceptual categories were generated by the analysis. Four conceptual categories were in the result of “JCA situation”, 4 conceptual categories were in the result of “Athletes using JCA”, and 7 conceptual categories were in the result of “JCA current difficulties”. Through the analysis it was revealed that: the JCA had occupational supports for both current and retired Olympic athletes; other supports such as psychological support were unclear due to the lack of psychological professionals in JCA and the difficulties collaborating with other sports organizations; and there are differences in tendencies of visiting JCA, financial situations, and career choices depending on Summer/Winter and Male/Female athletes.