The purpose of the present study was to examine the developmental experiences of high-performance coaches in Northern Ireland as a collective case study from an ecological perspective. Eight high-performance coaches from Northern Ireland were recruited and participated in semi-structured interviews. Each participant coached athletes at either World Championships, European Championships, Summer Olympic Games, Commonwealth Games, and/or professional levels. An ecological perspective was adopted to explore the barriers and supports for coaches at individual, interpersonal, organisational, and sociocultural levels throughout their coach development journeys. Data were analysed through theme development, refinement, naming, and triangulation. Findings are represented through the main themes and subthemes of: individual (previous athletic experience, engagement in experiential learning), interpersonal (networks, mentoring, non-sporting mentors), organisational (formal learning activities, varying levels governing body support, previous limitations of the high-performance system), and sociocultural (Northern Ireland’s unique political and geographical standing, dual nationality opportunities, and denominational perceptions of sports).