Roller derby is a unique and innovative phenomenon in the sporting landscape. Body image, gender policies, aggression/contact elements, music, art, and subversive and inclusive politics are all embraced to various degrees. Its growth was swift and significant – thousands of women around the world strapped on their skates and pushed themselves to meet the minimum skills requirements for joining a derby league. This unique sport was put in the (un)enviable position of somehow having done what governments and medical professionals had tried to achieve for years: to get people active who were inactive in the past, raise people's physical activity levels, and therefore (so the story goes) to improve their overall wellbeing and mental health. This article engages with interview transcripts with 12 derby skaters who chose to leave the sport in order to understand the complex social, cultural and personal forces at play in the relationship between sport and wellbeing. Drawing on feminist conceptualisations of care and movement, I explore the notion of “troubled derby subjectivities” to understand the ways in which the “sport” (including its style, music and affinities) provided a generative space for non-normative gendered subjectivities, embodied movement and “wellbeing”.