Bosworth lesions are fracture-dislocations of the ankle and are characterized by entrapment of the proximal segment of the fibula behind the posterior tubercle of the distal tibia. Treatment is challenging, mainly due to failure of a closed reduction. The aim of this study was to review the literature concerning this type of injury. A total of 103 patients with Bosworth fractures were included in the study. The analyzed studies yielded a total of 103 cases, of which 68% (n = 70) were male and 32% (n = 33) were female. Bosworth fractures are mainly due to accidental trauma (58.2%), sports-related injuries (18.4%), and traffic accidents (18.4%). More than 76% of the patients presented a Danis–Weber B fracture, 8.7% a type C fracture, and only 0.97% presented a type A fracture. In 92.2% of the patients, the attempted closed reduction was unsuccessful. A definitive treatment with open reduction and internal fixation (ORIF) was used in 96 patients (93.2%). The most frequent complication was post-traumatic arthritis (10.7%). Bosworth fractures are challenging. The available literature lacks adequate information about this fracture, and an approved standardized algorithm for treating such fractures is not available.