Polyphenols and other compounds found in cocoa and chocolate have therapeutic potential in the management of diabetes in humans. Polyphenol benefits have been proposed supported by in vitro studies, animal work, and clinical trials, which have been conducted mostly in healthy volunteers. The energy-dense formulations of many cocoa and chocolate products, which can be up to 50% sugar by weight, have given the perception that chocolate may be harmful through its contribution to obesity. A review of both clinical trial databases and published literature yielded 15 registered trials and 7 published studies. The published data interventions reported are diverse and vary widely in quality, including poor selection of control products or inadequate blinding procedures. There are also inconsistencies in reporting of data with limited information on the effect of cocoa and chocolate supplementation on weight and glycemic control despite the potential benefits reported with respect to the cardiovascular risk factors of endothelial function and lipids. More studies are required powered for primary clinical outcomes together with the development of standardized product formulations that optimize the dose of polyphenols within a palatable and energy-restricted product.