In Western countries, such as Australia and the UK, a significantly greater proportion of men (relative to women) are overweight and obese, yet relatively few weight loss interventions have been developed that sufficiently target men. This lack of male-focused programming may be in part because 'traditional' weight loss programs are unappealing for what is considered a 'hard-to-reach' population. One program that appears to have such appeal for men is the MAN v FAT Football (MVFF) program, based out of the United Kingdom, which is designed for men with a body mass index of (or greater than) 27.5. MVFF encourages men's participation in a community-based weight loss program that incentivizes weight loss through participation in a football league, and since 2016 MVFF has supported the weight loss efforts of several thousand men. Using MVFF as an exemplar, our aim was to derive insight into how men experience a male-only competitive, sport-based weight loss program. We recruited twenty-seven players (Mage ¼ 41.13, SD ¼ 9.93), and ten coaches (Mage ¼ 31.8, SD ¼ 11.55) from program locations throughout the United Kingdom. Using semi-structured interviews and thematic analysis, we identified several appraisal aspects of the program that players and coaches considered important, including the appeal of sport, competition on a level playing field, being part of a team, camaraderie, accountability, men sharing issues with other men, gender-sensitized environment, likeminded and similar men, and perceptions that traditional weight loss programs are tailored towards women. Player experiences (i.e., competence and enjoyment) and functional supports in the program (e.g., player handbook, weight loss coach) were reported to drive outcomes of effective weight loss and program retention. Interventions aiming to target men may be more successful working with rather than against formulations of identity such as masculinities, and this can be achieved by tailoring program content (e.g., messaging), settings (e.g., among men sharing similar characteristics such as body-type or goals), and mode of delivery (e.g., through organized sports, and leveraging competition to drive healthy behaviours).