Ankle Syndesmosis injuries represent only a minority of all ankle pathologies within elite football, however, are of particular interest to sports medicine practitioners due to their notable association with pain and disability. With the exception of several studies, there has been a shortfall of contemporary literature encapsulating diagnostic and prognostic indicators, as well as injury management approaches and their subsequent results. This presented case report summerises the conservative injury management and return to sport of an elite 29-year-old male professional football player, who sustained: acute full thickness tears of the anterior inferior tibiofibular ligament and anterior talofibular ligament, intrasubstance partial tears of the posterior inferior tibiofibular ligament and lower interosseous ligament, as well as suffering periosteal stripping of the superior extensor retinaculum from the anterior fibular margin, whilst concurrently managing a mild traumatic brain injury in the short-term. The presenting condition was sustained via an awkward landing from a jump, secondary to momentarily losing consciousness via ball-impact to the face from an opposing players’ cross. This caused the ankle/foot to become trapped beneath the player and forced into a hyper-dorsiflexed and externally rotated position. Clinical examination identified gross ankle effusion, pain on palpation around the anterolateral ankle, and a positive cluster of clinical special tests aimed to stress the anatomical structures comprising the syndesmosis. Magnetic Resonance Imagery (MRI) and subsequent review from an experienced foot and ankle specialist confirmed the diagnosis. Presented in this report is a literature-supported, detailed narrative of the examination process, conservative injury management and accompanying rehabilitation journey which ultimately resulted in the successful return to sport of the athlete.