The aim of this systematic review and meta-analysis was to determine the pattern of cognitive processing biases (ie, attentional, interpretation, and memory bias) towards headache and pain information observed in individuals with frequent or chronic headaches or migraines, compared with individuals without. We identified 11 studies (total N 5 841). Most studies (10 of 11) assessed attentional bias. For reaction time-based attentional bias (k 5 8), significant group differences were observed, with small (500 ms; g 5 0.200) to medium ($ 1000 ms; g 5 0.544) effects. Those with chronic headaches showed an absolute attentional bias towards headache and pain information. In 2 eye-tracking studies, both found significant medium-to-large group differences on initial orientation. Interpretation and memory bias research was also reviewed. A medium-to-large effect was found for interpretation bias (k 5 2; g 5 0.708), whereas the effect for recall memory bias (k 5 3) was not significant. Overall, the findings confirm an attentional bias for headache-related stimuli among people with headache, with some evidence for interpretation bias but equivocal evidence for a memory bias. For attentional biases, eye-tracking studies found evidence for biases in initial orienting. We provide suggestions for how to extend the current research to better understand cognitive biases in chronic headache.