Semistructured interviews were used in this study to learn about the challenges experienced by four groups of National Hockey League (NHL) players (N= 11): prospects (n= 3), rookies (n= 3), veterans (n= 2), and retirees (n= 3). The database is comprised of 757 meaning units grouped into 11 contextual challenges. From an additional quantitative analysis, the prospects and rookies emphasized challenges pertaining to scouting demands, training camp, increased athletic demands, team expectations, and earning team trust. The veterans spoke mostly of challenges including scouting demands, athletic demands, and team expectations. Retirees considered mostly challenges pertaining to team expectations, athletic demands, lifestyle, media demands, transactions, cross-cultural encounters, and playoffs. An expert panel ensured that the interview guide, data analysis, and the findings represented the participants’ experiences in the NHL. Recommendations for practitioners and researchers working with NHL players are proposed.