Isolated osteochondral fractures of the articular surface of the metatarsal head are rare injuries. To the best of our knowledge, there are less than ten reported cases of an acute isolated osteochondral metatarsal head fracture in the literature and no consensus has been reached regarding the best treatment. Both conservative treatment, through manipulation and close reduction, as well as open reduction and internal fixation were performed with good outcomes. We present a rare case of an isolated slipped-retroverted osteochondral fracture of the second metatarsal head treated by open reduction and internal fixation with a Herbert screw with an excellent outcome. The postoperative period was uneventful, and an excellent outcome was achieved. This case highlights the importance of a careful clinical and radiological evaluation for these rare lesions in order to avoid the undesirable sequelae of a missing diagnosis.