A retrospective review of 57 military patients undergoing ankle arthroscopy between 1999 and 2011 was performed. A case-note review of medical records was undertaken pertaining to military role, ankle injury sustained, mechanism, presenting symptoms and their duration. Arthroscopic findings were compared to findings on radiographs and MRI scans. At first presentation 23 patients had features of arthritis on radiographs. We found MRI was both highly sensitive (97.7%) and specific (93.4%) in detecting osteochondral defects (OCD). 16 of the patients had evidence of osteochondral injury. All OCDs picked up on MRI were confirmed at arthroscopy. Ankle injury may not be a benign injury in military personnel, with over half of these young patients having radiological features of osteoarthritis at presentation. We found MRI an effective tool for identifying occult injuries not seen on radiographs. Lateral ligament injury with associated gutter scarring can be successfully treated with arthroscopic debridement. This suggests pseudoinstability rather than a true mechanical instability as the main cause for patient's symptoms in this cohort.