Medical practice, monitoring and control guidelines enable standardization, assessment and quality improvement in healthcare. This often implies collecting and analyzing electronic medical records (EMRs) in order to calculate compliance metrics and support evidence-based decision-making. However, for these benefits to materialize a set of challenges must be overcome, including the complexity required to represent guidelines in such a way that compliance can be automatically determined with the aid of software; the combination of both structured and unstructured (narrative text) data; and cultural or political barriers. In this chapter, we present a strategy to overcome these challenges using three case studies in chronic disease for a developing country. As such, this work contributes an approach to enable the use of ICT-supported medical guideline evaluation, in order to contribute to a more reliable and context-dependent way of improving healthcare in developing countries in particular.