The 3rd edition of the International Classification of Headache Disorders replaced the term ophthalmoplegic migraine (OM) with Recurrent Painful Ophthalmoplegic Neuropathy (RPON) based on the presence of contrast enhancement of the involved cranial nerves on Gadolinium-enhanced magnetic resonance imaging. We review our experience and publications concerning ophthalmoplegia, migraine, and RPON. Majority of cases of acute ophthalmoplegia are associated with severe migrainous headaches. A positive history of migraine, increased severity of migraine headaches before the onset of ophthalmoplegia, and the close temporal association between migraine attacks and ophthalmoplegia all suggest an important role played by migraine in the causation of ophthalmoplegia. Enhancement of the involved cranial nerves may be due to the neuro-inflammatory cascade associated with migraine. OM should be considered along with RPON in differential diagnoses of painful ophthalmoplegic syndromes.