Background: Sensitivity of tissues can be measured by algometry. Decreased pressure pain thresholds over the cranio-cervical area are supposed to reflect signs of sensitization of the trigemino-cervical nucleus caudalis. A systematic review was conducted to assess the current scientific literature describing pressure pain threshold (PPT) values over the cranio-cervical region in patients with migraine, tension-type headache (TTH), and cervicogenic headache (CeH). A literature search was executed in three databases. The search strategy included the following keywords: migraine, TTH, CeH, PPT and algometry. A total of 624 papers was identified of which relevant papers were subsequently assessed for methodological quality. Twenty-two selected papers were assessed by two independent reviewers and the majority of studies scored low risk of bias on the selected items. Mean PPT values of several sites measured in the cranio-cervical region in patients with migraine, chronic TTH and CeH scored lower values compared to controls. The trapezius muscle (midpoint between vertebrae C7 and acromion) was the most frequently targeted site and showed significantly lower PPT values in adults with migraine (pooled standardized mean difference kPa: 1.26 [95%CI -1.71, −0.81]) and chronic TTH (pooled standardized mean difference kPa: -2.00 [95%CI -2.93, −1.08]). Most studies found no association between PPT values and headache characteristics such as frequency, duration or intensity. Further standardization of PPT measurement in the cranio-cervical region is recommended.