Different foods possess different bioactive compounds with varied antioxidant capacities. When foods are consumed together, the total antioxidant capacity of food mixtures may be modified via synergistic, additive, or antagonistic interactions among these components, which may in turn alter their physiological impacts. The main objective of this study was to investigate these interactions and identify any synergistic combinations. Eleven foods from three categories, including fruits (raspberry, blackberry, and apple), vegetables (broccoli, tomato, mushroom, and purple cauliflower), and legumes (soybean, adzuki bean, red kidney bean, and black bean) were combined in pairs. Four assays (total phenolic content, ferric reducing antioxidant power, 2,2-diphenyl-1-picrylhydrazyl, radical scavenging capacity, and oxygen radical absorbance capacity) were used to evaluate the antioxidant capacities of individual foods and their combinations. The results indicated that within the same food category, 13, 68, and 21% of the combinations produced synergistic, additive, and antagonistic interactions, respectively, while the combinations produced 21, 54, and 25% synergistic, additive, and antagonistic effects, respectively, across food categories. Combining specific foods across categories (e.g., fruit and legume) was more likely to result in synergistic antioxidant capacity than combinations within a food group. Combining raspberry and adzuki bean extracts demonstrated synergistic interactions in all four chemical-based assays. Compositional changes did not seem to have occurred in the mixture. Results in this study suggest the importance of strategically selecting foods or diets to maximum synergisms as well as to minimum antagonisms in antioxidant activity.