The increasing popularity of mHealth is a promising opportunity for pain self-management. Mobile apps can be easily developed, but understanding the design and usability will result in apps that can retain more users. This research aims at identifying, analyzing, and synthesizing the current state-of-the-art of: (a) the design approach and (b) usability assessment of pain management mobile applications. A systematic literature review was conducted on 27 studies retrieved from Medline, PubMed, EMBASE, Web of Science, and Scopus. The review revealed that most of the apps were for chronic pain. No app was specifically for men or for the elderly. None of the studies involved expert-based system inspection methods. Only one study used two different approaches of automated and empirical evaluation. We mapped the identified usability issues to ISO 9241-11 and ISO/IEC 25010, and aggregated the recommendations for improvement. Moreover, we also identified certain issues that are solely concerned with the patient’s behavior. We organized the issues into taxonomies of design considerations for building usable pain self-management mobile applications. As pain is prevalent among the elderly, pain management will be much needed while moving toward an aging society. However, we found that the involvement of the elderly in the development of pain management mobile apps is very minimal, which may affect the utility and usability of the apps.