Strawberries contain high levels of antioxidants, which have been correlated with a decreased risk of chronic disease. To more fully characterize the antioxidant profiles and possible associated health benefits of this fruit, the total free and bound phenolic, total flavonoid, and total anthocyanin contents of eight strawberry cultivars (Earliglow, Annapolis, Evangeline, Allstar, Sable, Sparkle, Jewel, and Mesabi) were measured. Cultivar effects on phenolic contents were compared with antioxidant capacities, as measured by the total oxyradical scavenging capacity (TOSC) assay, and to antiproliferative activities, as measured by inhibition of HepG2 human liver cancer cell proliferation in vitro. Free phenolic contents differed by 65% between the highest (Earliglow) and the lowest (Allstar) ranked cultivars. The water soluble bound and ethyl acetate soluble bound phenolic contents averaged 5% of the total phenolic content of the cultivars. The total flavonoid content of Annapolis was 2-fold higher than that of Allstar, which had the lowest content. The anthocyanin content of the highest ranked cultivar, Evangeline, was more than double that of the lowest ranked cultivar, Allstar. Overall, free phenolic content was weakly correlated with total antioxidant activity, and flavonoid and anthocyanin content did not correlate with total antioxidant activity. The proliferation of HepG2 human liver cancer cells was significantly inhibited in a dose-dependent manner after exposure to all strawberry cultivar extracts, with Earliglow exhibiting the highest antiproliferative activity and Annapolis exhibiting the lowest. No relationship was found between antiproliferative activity and antioxidant content.