Postgraduate Doctor of Medicine (DM) training at the University of the West Indies (UWI) has grown in response to the need to meet the regional requirements for high quality, competent clinical specialists. The progress of these programmes are examined from historical and health manpower development perspectives. More than 600 persons have been trained through the DM programmes at UWI, Mona and 89% of them continue to provide critical services in the region. Such statistics underscore the success of the programme in meeting the Caribbean Corporation in Health (CCH), UWI and Faculty of Medical Sciences (FMS) objectives. The relevance of the programme to the Caribbean’s needs is manifestly clear. Curriculum changes including a mandatory research component for all DM degrees reflect the evolution of training programmes as they adjust to current expectations of modern clinical practice and new emphases on evidence-based medicine and policies. Nevertheless, challenges exist including the deterioration of the physical plant for training, availability of training posts and funding of research. Monitoring, evaluation and quality assurance of existing programmes are to be continued.