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Sleep and headache have both generated curiosity within the human mind for centuries. The relationship between headache and sleep disorders is very complex. While Lieving in 1873 first observed that headaches were linked to sleep, Dexter and Weitzman in 1970 described the relationship between headache and sleep stages. ⋯ Patient education and lifestyle modification play a significant role in overall success of the treatment. Chronic tension-type headache and chronic migraine have high prevalence of insomnia and comorbid psychiatric disorders, which require behavioral insomnia treatment and medication if needed along with psychiatric evaluation. Apart from the abortive treatment tailored to the headache types, - such as triptans and DHE 45 for migraine and nonsteroidal anti-inflammatory medication for chronic tension-type headache, preventive treatment with different class of medications including antiepileptics (Topamax and Depakote), calcium channel blockers (verapamil), beta blockers (propranolol), antidepressants (amitriptyline), and Botox may be used depending upon the comorbid conditions.