It has been suggested that the objectives of elite sport and positive youth development are sometimes in conflict (Fraser-Thomas & Strachan, in press). For example, elite-youth sport coaches may justify sitting players to secure the team’s win, with detrimental consequences to benched players’ confidence and self-image. Recently, there has been growing interest in an athlete-centred coaching philosophy – where attention is devoted to the overall development of both the athlete and the person, by providing athletes with autonomy, fostering a mastery-oriented environment, and creating partnerships within the coach-athlete relationship (Kidman & Lombardo, 2010; Mallet, 2005). In this study, I used an auto-ethnographic research design (Ellis & Bochner, 2000) to examine, understand, and negotiate my own experiences implementing an athlete-centred coaching philosophy as the head coach of a ‘AAA’ minor hockey team, within the broader social context of elite youth sport and positive youth development. Using self-reflection and journaling throughout the 2013-2014 season, I identified several challenges in my aims to facilitate athletes’ optimal performance and personal development including balancing the needs of individuals with the needs of the team given the pressures to win, creating a mastery-oriented environment within a results driven sporting culture, and developing the athletes individually while in charge of a team of seventeen players. Primary successes included fostering autonomy early in the season during the training camp, decreasing the pressures to win in important games, and developing my overall abilities as a coach throughout the season. Findings highlight the pervasive influence of winning expectations within the elite youth sport culture, and shed light on the complex ways in which these expectations interacted with my intended coaching approach throughout the season. Implications for coach education (e.g., the value of elite youth sport coaches self-assessing and developing their own skills) and future research are addressed.