Understanding the complexity of coaching in disability sport remains a pressing concern. While interest in disability sport continues to grow there is a relative lack of insight into coaching in this context, particularly research which illustrates a ‘grounded’ perspective on practice. As a result, coaching in disability sport is critically under-theorised, and we know comparatively little of the nature of coaching in different disability sport contexts (Townsend, Smith & Cushion, 2016). There have been longstanding calls to understand coaches’ learning and development in disability sport (DePauw, 1986), and as a result there is a small, but growing, body of literature which has begun to explore the unique considerations of coaching in disability sport. Such considerations include the informal and unstructured nature of coach learning (e.g. McMaster, Culver & Werthner, 2012; Duarte & Culver, 2014; Taylor, Werthner & Culver, 2014; Taylor, Werthner, Culver & Callary, 2015), the lack of disability-specific coach education (e.g. Cregan, Bloom & Reid, 2007; Douglas et al., 2016; Douglas & Hardin, 2014), and the complex and multifaceted role of coaches in disability contexts (e.g. Tawse, Bloom, Sabiston & Reid, 2012; DePauw & Gavron, 1991), all of which invite and encourage comparisons with the narrative presented below. More recent research however, has challenged the lack of critical insight in disability coaching research (e.g. Townsend et al., 2016), arguing that the research is characterised by a normative focus that downplays the inter-connections between disability and cultural contexts such as sport. The lack of consideration of disability is an important theoretical ‘gap’, as Smith and Bundon (2016) argue, having a grasp on how disability is explained and understood is vital for individuals working with disabled people in any context, especially in coaching where practice is fundamentally shaped by our working understanding of disability (cf. DePauw, 2000). It is the purpose of this chapter, then, to encourage practitioners and researchers to examine their understandings of disability in the first instance, as a basis for developing coaching practice. What follows are reflections from Derek Morgan, Head Coach of the England Learning Disability Cricket squad, but, first, some context about the team.