Terminalia spp. have long been used medicinally in traditional healing systems, including for the treatment of cancers. Several species, including T. chebula, T. bellerica, and T. ferdinandiana, have been reported to have potent antiproliferative activities against multiple cell lines. A number of anticancer mechanisms have been studied, with the induction of apoptosis consistently reported. Several of those studies correlated the anticancer properties of these plants with their high antioxidant and tannin contents. Notably, many of these components have potent anticancer properties when tested alone, indicating that they may contribute to the anticancer properties of this genus. Recent studies have also identified other notable compounds (including the combretastatins and other stilbenes) that have potent anticancer activity and it is likely that these may also contribute to the anticancer properties of Terminalia spp. This chapter reviews the current knowledge regarding the phytochemistry and anticancer properties of this genus with the aim of stimulating and focusing further study in this field.