A 31-year-old male who works as a sports physiotherapist sustained a right ankle pronation injury whilst playing football. He did not seek immediate medical attention. He then presented 5 weeks later to the orthopaedic clinic complaining of deteriorating pain associated with ankle swelling and anterolateral ankle pain. He underwent an MRI that was reported with a small intra-articular effusion, a prominent os trigonum, lateral collateral ligamentous attenuation/fibrosis, and features of chronic posterior impingement. At the time, he was managed nonoperatively with a walking boot for 2 weeks and protected weight bearing. In 2018, he noted persistent posterior ankle pain. He did not sustain any new trauma. A right ankle CT scan demonstrated a malunion/partial union of the medial margin of the talus and secondary degenerative changes (see Figure 7). There was also still the presence of a prominent os trigonum with sclerotic changes associated with it. He was again managed nonoperatively with a walking boot and protected weight bearing during periods of exacerbation. He was able to return back to sporting activity once pain symptoms improved.