Education evaluation has become increasingly important in the English-speaking Caribbean. This has been in response to assessing the progress of four regional initiatives aimed at improving the equity, efficiency, and quality of education. Both special interest groups and local evaluators have been responsible for assessing the progress of education and providing an overall synthesis and summary of what is taking place in the English-speaking Caribbean. This study employed content analysis to examine the indicators used in these education evaluation studies since the declaration of the Caribbean Plan of Action 2000–2015 to determine these indicators’ appropriateness to the Caribbean context in measuring education progress. Findings demonstrate that the English-speaking Caribbean has made strides in operationalizing quality input, process, and output indicators; however quality outcome indicators beyond test scores are yet to be realized in a systematic manner. This study also compared the types of collaborative partnerships in conducting evaluation studies used by special interest groups and local evaluators and pinpointed the one that appears most suitable for special interest groups in this region.