The prevalence of chronic daily headache (CDH) worldwide is 4–5%. Treatment for CDH with prophylaxis and abortive medications is often delayed, increasing disease severity. Consequently, increased usage of over-the-counter (OTC) analgesics can lead to medication overuse headache (MOH). This study aimed to assess factors affecting OTC analgesic overuse causing headaches. Methodology: A cross-sectional structured survey was conducted using voluntary response sampling. Among 1177 respondents, 459 individuals with headache were enrolled in the study. Results: Most participants were female (73.5%), almost half were aged 20–39 years (48.1%), and over half used OTC analgesics (56%). A significant association was found between OTC analgesic overuse and factors, such as chronic disease (p
= 0.007), working status (p
= 0.015), smoking (p
= 0.02), headache frequency >15 days per month (p
= 0.000), migraine-type headache (p
= 0.01), preventive medicine use (p
= 0.018), and emergency department visit (p
= 0.018). Conclusion: OTC analgesic overuse among individuals with headache is affected by several factors, including the presence of chronic diseases, working status, smoking, and migraine-type headaches. However, preventive medicine and emergency department visits were considered to have protective effects. Health care providers should screen patients for MOH, increase their awareness, and follow MOH guidelines to treat chronic headache.
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