Twenty-nine healthy volunteers aged 47–69 years old were randomly assigned to a 28-day oral intake of different dark chocolate (DC) formulations. The main group received daily 30 g of proprietary lycopene-containing (L-tug) lycosome formulation of DC with enhanced bioavailability of cocoa flavanols. Two control groups daily consumed either 30 g of regular DC alone or along with 7 mg of lycopene, which corresponds to the amount of lycopene ingested with L-tug formulation. It was found that L-tug was more efficient in reducing diastolic blood pressure (mean value of −6.22 mmHg, 95% CI: 5.00, 8.00) when compared with the regular DC group (−3.00 mmHg, P < 0.05) or the group which ingested the DC and lycopene as two separate formulations (mean reduction of −4 mmHg, 95% CI: 2.47, 6.00, P = 0.0262). Only marginal superiority for L-tug formulation in the reduction in systolic blood pressure was seen. However, the L-tug formulation was the only formulation of DC which affected serum lipids. There was a reduction in total cholesterol (from median 228.00 mg/dL [95% CI: 206.2, 242.5] to 187.00 mg/dL [95% CI: 166.2, 202.2, P < 0.05]) with corresponding decline of low-density lipoprotein (LDL) cholesterol (from a median of 166.00 mg/dL [95% CI: 130.8, 177.0] to 151.00 mg/dL [95% CI: 122.8, 167.4; P < 0.05]) at the end of the intervention period. Similar decline was seen in serum triglycerides (P < 0.05). Serum high-density lipoprotein (HDL) cholesterol, glucose levels, and C-reactive protein (CRP) values remained statistically unchanged in all study groups throughout the intervention period. A superior biological activity of the L-tug lycosome formulation of DC extending beyond its antihypertensive effect to lipid-lowering ability opens up new possibilities for the use of DC for health purposes helping to reduce daily caloric intake without compromising on the health benefits of DC consumption.