Background: Mobile and web technologies are becoming increasingly used to support the treatment of chronic pain conditions. However, the subjectivity of pain perception makes its management and evaluation very difficult. Pain treatment requires a multi-dimensional approach (e.g., sensory, affective, cognitive) whence the evidence of technology effects across dimensions is lacking. This study aims to describe computerised monitoring systems and to suggest a methodology, based on statistical analysis, to evaluate their effects on pain assessment. Methods: We conducted a review of the English-language literature about computerised systems related to chronic pain complaints that included data collected via mobile devices or Internet, published since 2000 in three relevant bibliographical databases such as BioMed Central, PubMed Central and ScienceDirect. The extracted data include: objective and duration of the study, age and condition of the participants, and type of collected information (e.g., questionnaires, scales). Results: Sixty-two studies were included, encompassing 13,338 participants. A total of 50 (81%) studies related to mobile systems, and 12 (19%) related to web-based systems. Technology and pen-and-paper approaches presented equivalent outcomes related with pain intensity. Conclusions: The adoption of technology was revealed as accurate and feasible as pen-and-paper methods. The proposed assessment model based on data fusion combined with a qualitative assessment method was revealed to be suitable. Data integration raises several concerns and challenges to the design, development and application of monitoring systems applied to pain.