Ankle injuries are a very common cause of patient visits to the primary care units and emergency departments. Although the most frequent ones are lateral ligament sprains, peroneal tendon subluxations have the same inversion mechanism and are described as one of the main causes of lateral ankle pain and instability. They are often missed during the acute phases as they are misdiagnosed as ankle sprains since both injuries share similar mechanisms and often occur in athletes and patients with high sports activity.We present two different cases of peroneal tendon dislocation that illustrate how this pathological condition may be present under different circumstances. We aim, through these cases, to provide clinical awareness and help improve earlier diagnosis of this condition; we also demonstrate the effectiveness of surgical reattachment of the upper retinaculum that two of our patients underwent.