: Cognitive dysfunction is frequently observed in chronic migraine (CM) patients, but the contributing medical and psychological factors remain unclear. This study investigated associations between the cognitive reserve and medical, psychological, and lifestyle factors in individuals with CM. : A retrospective review was conducted at a tertiary referral center in Taiwan. Cognitive function was evaluated via the mini-mental state examination (MMSE), while anxiety and depression were evaluated via the Beck Anxiety and Depression Inventories. Clinical variables included monthly headache days, headache intensity (numerical rating scale), migraine-related disability, and use of preventive medications. Multivariable linear regression analyses were performed to identify independent predictors of the cognitive reserve after adjusting for relevant covariates. Among 50 participants (86.0% women; mean age 42.48 ± 13.47 years), six (12.0%) exhibited objective cognitive impairment (MMSE < cutoff). After a covariate adjustment, higher headache intensity was significantly associated with a lower cognitive reserve in anxiety and depression models. Patients with objective cognitive impairment reported significantly higher levels of pain, anxiety, and depression. : The headache intensity, anxiety, and depression were significantly linked to a lower cognitive reserve in CM patients. These findings highlight the importance of incorporating routine psychological and cognitive assessments in CM care and suggest potential targets for integrative treatment strategies.