This study investigated the relationship between health status (i.e., physical well-being and quality of life), sleep disorders (e.g., insomnia, sleep-related depression and anxiety), and musculoskeletal pain in the craniomandibular and cervical spinal regions. The number of painful body areas below the cervical spine (i.e., widespread pain) was also taken into account. Two questionnaires, viz., the RAND 36-item Health Survey Questionnaire and the Dutch Sleep Disorders Questionnaire (SDQ), were administered to 103 persons who could unequivocally be classified into one of four mutually exclusive groups: No pain, craniomandibular pain (CMP), cervical spinal pain (CSP), and both CMP and CSP. Body drawings were used for the self-report of widespread pain. Multivariate analysis of variance showed effects of gender, group, and widespread pain on the questionnaire scales; not of age. As shown by univariate analysis of variance, men suffered more from sleep apnea than did women. No other gender differences were found. Simple contrast analyses following univariate analyses of the group and widespread pain effects showed that, in general, more questionnaire scales, both of the RAND-36 and of the SDQ, reached statistical significance with an increase in the number of painful areas. It was concluded that both musculoskeletal pain in the trigemino-cervical area and widespread body pain are associated with an increased impairment of health status. Also, sleep disorders are frequently found in patients with chronic pain in the craniomandibular and cervical spinal regions as well as in patients with widespread pain. The more painful areas there are, the likelier it is that sleep disorders are present.