Two oxidation systems were examined for the oxidation of three groups of phenolic antioxidants; five cinnamic acids, two benzoic acids, and two phenols characteristic of olive fruits. Periodate oxidation, which is reported to produce products similar to polyphenol oxidase, was contrasted with the reactivity of the Fenton system, an inorganic source of hydroxyl radicals. Reaction products were identified as various quinones, dimers, and aldehydes, but the nature of the products differed between the two oxidation systems. Structure-activity effects were also observed for the different phenols. All cinnamic acids in this study reacted with the Fenton reagent to produce benzaldehydes as the main products, with the exception of 5-caffeoylquinic acid. In contrast, periodate oxidation gave no reaction with some of the cinnamic acids. Quinone formation was observed for the two compounds, caffeic acid and 5-caffeoylquinic acid, possessing o-hydroxy groups. Caffeic acid was unusual in that dimer formation was the main initial product of reaction. Benzoic acids were readily oxidized by both systems, but no identifiable products were isolated. Oleuropein was oxidized by both oxidants used in this study, resulting in quinones in each system, whereas little or no oxidation of tyrosol was observed. This highlights the importance of conjugation between the alkene double bond and the hydroxy group. The results question the validity of many existing methods of testing antioxidant activity.