The purpose of this study is to provide a detailed description of the anatomy and radiology of the medial sleeve and present an approach in its management among elite athletes. Five cases of elite athletes who underwent treatment for a medial sleeve injury of which the diagnosis was confirmed through physical examination and additional magnetic resonance imaging scan are described in this study. Two patients presented with isolated medial sleeve injuries, while the other three patients suffered from concomitant ankle injuries. Non-operative treatment consisted of relative rest, soft cast immobilization and mobilization in a walking boot or kinesiotape which was successful in four of the cases with regard to the medial sleeve. One patient underwent surgery due to syndesmotic instability. Another patient presented with combined medial and lateral ankle instability which was treated surgically with an open medial and lateral ligament repair. All patients were able to return to their pre-injury sports and at the time of the last follow-up were still playing in their pre-injury level of competition. Medial sleeve injuries of the ankle in elite athletes should be considered in the differential diagnosis for athletes presenting with medial ankle pain. Inherent knowledge regarding anatomy is essential when guiding the management of these injuries which can be treated successfully with a non-operative approach consisting of relative rest, immobilization, kinesiotape and physical therapy. In case of persistent medial instability or rotational instability, surgical repair is a viable treatment option. Both modalities allow athletes to return to the pre-injury level of competition. However, early diagnosis is crucial to minimize the delay of appropriate treatment and avoid potential residual symptoms. Level IV.