Scope: To evaluate whether increases in the consumption of cardioprotective food groups (virgin olive oil, nuts, fruits/vegetables, legumes, whole grains, fish, and wine) are associated with improvements in high-density lipoprotein (HDL) functions in high cardiovascular risk subjects. Methods and Results: The association between 1-year changes in food group consumption and HDL functionality traits in 296 high cardiovascular risk subjects is assessed. Increases in virgin olive oil (10 g d –1 ) and whole grain consumption (25 g d –1 ) are associated with increments in cholesterol efflux capacity (+0.7%, P = 0.026, and +0.6%, P = 0.017, respectively). Increases in nut (30 g d –1 ) and legume intake (25 g d –1 ) are linked to increments in paraoxonase-1 activity (+12.2%, P = 0.049, and +11.7%, P = 0.043, respectively). Legume intake increases are also related to decreases in cholesteryl ester transfer protein activity (–4.8%, P = 0.028). Fish consumption increments (25 g d –1 ) are associated with increases in paraoxonase-1 activity (+3.9%, P = 0.030) and declines in cholesteryl ester transfer protein activity (–1.6%, P = 0.021), HDL cholesterol concentrations (–1.1%, P = 0.039), and functions related to HDL levels (cholesterol efflux capacity, –1.1%, P = 0.010). Conclusion: Increases in the consumption of virgin olive oil, nuts, legumes, whole grains, and fish (achievable through a regular diet) were associated with improvements in HDL functions in high cardiovascular risk subjects.