A plethora of work has identified forms and sources of gender inequality in sport coaching. Quantitative studies with psychological framings dominate the literature. However, a smaller and more recent body of qualitative work has identified structural gender hierarchies as the root of inequalities, specifically the prevalence of hegemonic masculinity. Fewer studies have contextualised understandings of women’s experiences of this, particularly at grassroots levels and there is little acknowledgement of a notable shift in the visibility of women’s power and presence in society including sport. Thus, in this study Gill’s (2007) postfeminist sensibility was used to examine seven female coaches’ experiences of various grassroots sports settings, specifically what might be novel in women’s contemporary coaching experiences, but also to acknowledge any persistent structural inequalities. Findings suggest that while female coaches are continually facing challenges borne out of dominant forms of masculinity which remain deeply rooted in sport cultures, they are actively contesting and navigating these by drawing upon performed masculinities. Consequently, new femininities have emerged, but these are fragile, often misinterpreted and can lead to women struggling to progress their coaching careers. Future work in this field should look to develop the use of postfeminist lenses in similar ways, to further identify new(er) femininities which have the potential to grow and develop women’s representation in coaching.