Chronic primary headache is a prevalent health problem worldwide, and its impact on mental health and psychosocial functioning is well documented. Studies examining the emotional component of chronic headache have indicated that headache sufferers present significantly higher levels of depression, anxiety and anger in comparison with headache-free individuals. The main aim of this study was to examine the emotions associated with the experience of chronic headache and its relationship with headache severity and headache-related disability. In particular, it was proposed to identify the types of emotion that are prominent in this patient group, the role of anger in chronic headache, and what strategies headache sufferers use most frequently to regulate their emotions, in comparison with non-headache controls. A total of 104 individuals took part in this study. Of those, 57 were chronic headache sufferers and 47 constituted the control group. Participants were asked to complete a questionnaire package comprising a demographic cover sheet and a range of measures assessing headache-related disability, basic emotions, emotion regulation strategies, anger, depression and anxiety. Results indicated that headache sufferers experienced higher levels of emotional disturbance (including depression, anxiety and anger) than headache-free individuals. Affective distress was found to be associated with perceived emotional and functional headache-related disability and, to a lesser extent, with headache severity. Depression symptoms, anger and the use of internal-dysfunctional strategies were found to be significant predictors of headache-related disability, while the use of internal-dysfunctional emotion regulation strategies was found to be a significant predictor of headache severity. These findings suggest that negative emotions are an integral part of the experience of chronic headache and need to be addressed in treatment.