The purpose of the current study was to investigate the similarities and differences of retirement experiences of professional versus high performance amateur athletes determined by participation statistics in Canada. Results were obtained through qualitative interviews with 5 retired professional hockey players, and 4 retired high performance amateur rugby players who retired from sport within the last 15 years. Interview questions were based on Wylleman and Lavallee’s theoretical model of transitions faced by athletes at athletic, individual, psychosocial, and academic/vocational levels. The research concluded that there are many similarities experienced by professional hockey and high performance amateur rugby athletes regarding their sport retirement. However, there are also some considerable differences experienced by these athletes. Additional research may lead to awareness of coping resources and supports available to athletes experiencing retirement from various sports to help improve preparation and the quality of retirement experiences.