Sleep is an essential biological process that supports survival, tissue repair, cognitive functioning, and memory consolidation. Pain, an inherent part of human experience, often coexists with sleep disturbances. While subjective evaluations are common in sleep research, objective measures such as polysomnography provide critical insight into actual sleep quality. This study aimed to examine the interplay between orofacial pain (OFP), headache (HA), and sleep quality using both self-reported and instrument-based assessments. A secondary goal was to explore whether poor sleep results primarily from pain or is influenced by psychological factors like anxiety, stress, and depression. Participants with OFP and HA from the Outpatient Clinic for Temporomandibular Disorders at Wroclaw Medical University, Poland, underwent one night of video-polysomnography. Complementary questionnaires were used to evaluate sleep patterns, pain severity, headache characteristics, and psycho-emotional status. Objective sleep parameters measured through polysomnography did not show a significant relationship with the intensity of OFP or HA. In contrast, subjective sleep assessments demonstrated a clear association with reported pain levels. Pain severity was also closely linked to elevated depression, anxiety, and stress scores. Psychological factors significantly influence the perception of OFP and HA and may contribute to reduced subjective sleep quality, insomnia, and daytime drowsiness. Effective management of these conditions should include a thorough assessment of emotional well-being, as mood disturbances can profoundly affect symptom severity and response to treatment.