Despite thoracic outlet syndrome (TOS) being first described early in the 19th century, the subsequent literature seems limited, focusing on case reports and investigations providing little assistance in the management of equivocal presentations. Best practice clinical management, with little evidence base, poses great challenges for clinicians in deciding how to manage TOS, when to operate and which procedure should be undertaken. Furthermore, the implications of TOS and its surgical effects are poorly documented, with little evidence in the literature as to the impact of surgical intervention on athletes and their physiology or function. This paper describes a clinical example of TOS highlighting salient issues and examining the evidence to guide clinical management at each stage, in the case of a 26-year-old professional football player who suffered an acute onset of unilateral right shoulder to bicep pain associated with tingling in the hand. Clinicians managing similar cases in the future will have a reference point to assist their diagnosis, management and promote much needed research to further our understanding of this difficult syndrome.