The current scoping review aimed to map current literature investigating the relationship between pain extent extracted from pain drawings with clinical, psychological, and psycho-physiological patient-reported outcome measures in people with pain. Electronic databases were searched for cross-sectional cohort studies that collected pain drawings using digital technology or a pen-on-paper approach and assessed for correlations between pain extent and clinical, psychological or psycho-physical outcomes. Data were extracted by two different reviewers. The methodological quality of studies was assessed using the Newcastle–Ottawa Quality Assessment Scale. Mapping of the results included: 1, description of included studies; 2, summary of results; and 3, identification of gaps in the existing literature. Eleven cross-sectional cohort studies were included. The pain disorders considered were heterogeneous, ranging from musculoskeletal to neuropathic conditions, and from localized to generalized pain conditions. All studies included pain and/or pain-related disability as clinical outcomes. Psychological outcomes included depression and anxiety, kinesiophobia and catastrophism. Psycho-physical measures included pressure or thermal pain thresholds. Ten studies were considered of high methodological quality. There was heterogeneity in the associations between pain extent and patient-reported outcome measures depending on the pain condition. This scoping review found that pain extent is associated with patient-reported outcome measures more so in patients presenting with musculoskeletal pain, e.g., neck pain or osteoarthritis, rather than for those with neuropathic pain or headache.