Chondromyxoid fibroma (CMF) is a very rare entity, accounting for <1% of all bone tumours. So far, only 4 cases have been reported with the orbit as primary location. Here, we present a case of orbital CMF with periocular pain as the presenting symptom and as the only symptom when the tumour recurred after surgery. A 41-year-old man underwent a CT scan and later an MRI as part of evaluation for left periocular pain that had persisted for a year. Clinical examination was normal. CT and MRI revealed an irregular mass in the lateral part of the left orbital roof. The tumour was removed by curettage, and histopathological examination showed a CMF. The pain was absent for 3 months. A second MRI 5 months postoperatively revealed a recurrence, which was removed surgically, resulting in pain alleviation. In conclusion, CMF is a potential cause of periocular pain, and persistent periocular pain with normal clinical findings should warrant a CT or MRI scan.