The aim of this study was to assess the ability of different wines – a sweet red, a dry red, a sweet white, and a dry white – to scavenge the stable 1,1’-diphenyl-2-picryl-hydrazyl radical (DPPH.) and to determine their phenolic composition. Both red wines contained, apart from anthocyanins, also higher concentration of total phenolics, tartaric esters, and flavonols than the two white wines. All wines exhibited scavenging activity analogous to their total phenolic content. However, their phenolics differed in antiradical potency, which was visible in their EC50 values. The dry red wine, Xinomavro, had a lower EC50 value, indicating the higher antiradical potency of its phenolics. The scavenging capacities of phenolic extracts from Xinomavro red wine on hydroxyl radicals, superoxide radicals, and singlet oxygen were also assessed. Wine total extract was fractionated by extraction, and each of the three fractions was then subfractionated by column chromatography into two subfractions. Wine total extract, and its fractions and subfractions exhibited scavenging capacity on hydroxyl radicals, superoxide radicals, and singlet oxygen, indicating the activity of many wine phenolics. The most active wine extracts towards hydroxyl radicals were characterized by the high peaks of flavanols, anthocyanins and flavonols in their HPLC-DAD chromatograms. The most active extract towards superoxide radicals was rich in flavanols and anthocyanins. The characteristic phenolics of the most active wine extracts towards singlet oxygen were flavanols, flavonols and phenolic acids. The ability of all red wine phenolic extracts to scavenge singlet oxygen, along with hydroxyl and superoxide radicals, emphasizes its health functionality.