Cluster headaches are a series of short, excruciating, and unilateral pain that happens for a short period at a time over days, weeks, or months and may awake people from sleep. It is situated behind, in, or around one eye only with possible radiation to the forehead at the same side. Cluster headache is characterized by many ocular features. However, extraocular muscle involvement is unusual in this type of headache. We present a case of chronic cluster headache associated with diplopia due to oculomotor nerve palsy in a 24-year-old man, which responded successfully to oral steroid. This presentation is rare. Therefore, ophthalmologists and neurologists should consider it in their list of a differential diagnosis. A short course of oral prednisolone has a role in the management of patients in such cases.