Regular cocoa consumption has been shown to improve blood pressure (BP), insulin sensitivity, and lipid levels in patients with type 2 diabetes (T2D), using up to 100 g of chocolate or 54 g of cocoa. These effects, attributed to cocoa flavanols, would be beneficial for patients with T2D if they could be achieved by a usual serving size of flavanol-rich cocoa. Forty-two hypertensive patients with T2D (stable pharmacological treatment, with good adjustment for glucose metabolism, lipids, and BP) ingested capsules with 2.5 g/day of a flavanol-rich cocoa or cocoa-free capsules for 12 weeks in a double-blinded, randomized, placebo-controlled study with parallel group design. Participants had to maintain diet, lifestyle, and medication. Before and after intervention, fasting blood samples were collected; BP and nutritional status were investigated. Cocoa treatment did not affect BP, nor glucose metabolism (glucose, HbA, insulin, HOMA-IR) and lipids (triglycerides, total cholesterol, low-density lipoprotein cholesterol, high-density lipoprotein cholesterol). Body weight, fat mass, and nutrient supply remained unchanged. Changes in the placebo group did not occur. Regular intake of a usual serving size of flavanol-rich cocoa does not improve cardiometabolic parameters in stably treated patients with T2D and hypertension. As the medication modulates partly the same targets as cocoa flavanols, future studies should focus on the preventive effect of cocoa against diabetes and other cardiometabolic diseases in individuals with preexisting abnormalities that do not require any pharmacological treatment.