Background <p>Migraine is prevalent among women of childbearing age and is associated with increased long-term cardiovascular and cerebrovascular risk. Pregnancy, a hypercoagulable state, may potentiate these risks. This study aimed to quantify the association between migraine or pregnancy-related headaches and cerebrovascular and cardiovascular events during pregnancy and the postpartum period.</p> Methods <p>We conducted a PRISMA-compliant systematic review and meta-analysis of observational studies comparing pregnant women with and without migraine or pregnancy-related headaches. PubMed, Scopus, and Web of Science were searched through May 8, 2025. Adjusted odds ratios (ORs) were pooled using random-effects models.</p> Results <p>Twelve studies encompassing 94,195,776 pregnancies met the inclusion criteria. Migraine was associated with markedly increased odds of all strokes and transient ischemic attacks (OR 10.45; 95% CI 4.27–25.57) and ischemic stroke (OR 7.14; 95% CI 2.51–20.31). Hemorrhagic stroke risk was elevated but not statistically significant overall (OR 2.25; 95% CI 0.99–5.18), while subarachnoid hemorrhage showed a 69% increased odds. Regarding cardiovascular events: myocardial infarction risk increased by 96%, peripartum cardiomyopathy odds were 2.68-fold (95% CI 1.73–4.14), and spontaneous coronary artery dissection odds were 9.21-fold higher (95% CI 3.72–22.82). All included studies were rated as “good” quality by the Newcastle-Ottawa Scale.</p> Conclusions <p>Migraine and pregnancy-related headaches are independent risk factors for a broad spectrum of cerebrovascular and cardiovascular events during pregnancy and the puerperium. These findings highlight the need for heightened clinical surveillance, targeted cardiovascular risk counselling, and multidisciplinary management strategies for this population.</p>