Post-craniotomy headache (PCH) is a common postoperative complication, and some of these patients progress to chronic PCH (CPCH). We aimed to identify clinical variables associated with PCH and its progression to CPCH, especially possible associations between age and sex differences. Therefore, we examined clinical information on PCH using the Clinical Data Warehouse over 10 years. Of the 1326 patients included, 927 patients (69.9%) experienced PCH. In multivariate analysis for PCH, age was inversely related to risk (p = 0.003), and being female showed a significant association with an increased risk of PCH (p = 0.002). There was also a significant inverse relationship between age and severity of the worst headache, with younger female patients reporting greater severity of the worst headache (p < 0.001). Of the 927 patients who experienced PCH, 319 (34.4%) progressed to CPCH. Sex was a significant factor, with females having a higher risk of developing CPCH compared to males (p < 0.001). In addition, the presence of preoperative headaches significantly increased the risk of CPCH (p = 0.001). The occurrence of PCH is associated with younger age and female sex. In particular, female sex and preoperative headaches increased the risk of developing CPCH. These clinical factors should be considered in patients undergoing neurosurgery.