Prevention of diabetes mellitus type 2 (DMT2) through the diet is receiving a growing interest and cocoa because of its polyphenolic compounds, mainly flavanols, has become an important potential chemopreventive natural agent. Cocoa and its main flavanols might contribute to prevent or delay diabetes mellitus type 2 by modulating insulin secretion in β-pancreatic cells and targeting insulin-sensitive tissues because of their insulin-like activity or through the regulation of key proteins of the insulin signaling route. Among other actions, cocoa flavanols have been proved to enhance glucose uptake through the promotion of glucose transport, to repress glucose production, or to improve lipid metabolism. Nevertheless, the molecular mechanisms of action involved in these effects are not fully understood and many points remain to be clarified. This review provides insights into the molecular machinery of the chemopreventive activity of cocoa and its flavanols by compiling cell culture and animal models studies, as well as evidence from human interventional trials.