Concerns about gender inequalities in longevity, particularly premature male mortality, have prompted a range of innovative approaches to health promotion work with men dating back to the 1980s. In developing such work, sport, and football in particular, has emerged as a gendered cultural field that has utility for engaging men in health initiatives. Evaluations of such work, whilst few in number, have shown that health initiatives using football settings, football based interventions, or even football club branding, can have positive impact on various health measures in the short and the longer term. However, little work to date has looked at the underlying mechanisms that generate success in such projects. This paper presents secondary analysis of data collected during the evaluation of the Premier League Health (PLH) programme specifically focusing on these underlying mechanisms and how/where gender (masculinities) appears in these processes. We draw on interview data with sixteen staff who had been involved in the delivery of the PLH initiative and fifty-eight men who took part. Thematic analysis highlighted two overarching (and underpinning) themes: 'Trust', what processes it was key to and how it was developed and sustained; 'Change', including what it was facilitated by and what impact it had. The paper adds to our understanding of how active listening, flexibility and sustained engagement are key to sports based projects generating success. Furthermore, it demonstrates how the physicality and sociability of involvement, rather than any direct focus on 'health' was important in acting as a spring-board for facilitating reflection and aiding lifestyle changes for the men in line with PLH programme desired outcomes.