Olive pomace oil (OPO) is mainly a source of monounsaturated fat together with a wide variety of bioactive compounds, such as triterpenic acids and dialcohols, squalene, tocopherols, sterols and aliphatic fatty alcohols. To date, two long-term intervention studies have evaluated OPO’s health effects in comparison with high oleic sunflower oil (HOSO, study-1) and sunflower oil (SO, study-2) in healthy and cardiovascular risk subjects. The present study integrates the health effects observed with the three oils. Two randomized, blinded, cross-over controlled clinical trials were carried out in 65 normocholesterolemic and 67 moderately hypercholesterolemic subjects. Each study lasted fourteen weeks, with two four-week intervention phases (OPO versus HOSO or SO), each preceded by a three-week run-in or washout period. Regular OPO consumption reduced total cholesterol (p = 0.017) and LDL cholesterol (p = 0.018) levels as well as waist circumference (p = 0.026), and only within the healthy group did malondialdehyde (p = 0.004) levels decrease after OPO intake versus HOSO. Contrarily, after the SO intervention, apolipoprotein (Apo) B (p < 0.001) and Apo B/Apo A ratio (p < 0.001) increased, and to a lower extent Apo B increased with OPO. There were no differences between the study groups. OPO intake may improve cardiometabolic risk, particularly through reducing cholesterol-related parameters and waist circumference in healthy and hypercholesterolemic subjects.