Tephorosia purpurea subsp. apollinea was extracted with methanol and n-hexane to obtain sub-fractions. The chemical compounds identified with GC-MS and HPLC in T. purpurea subsp. apollinea extracts showed antioxidant and anticancer properties. The antioxidant and anticancer activities were investigated using DDPH and ABTS assays, and MTT assay, respectively. Stigmasta-5,24(28)-dien-3-ol, (3 β,24Z)-, 9,12,15-octadecatrienoic acid methyl ester, phytol, chlorogenic acid, and quercetin were the major chemical compounds detected in T. purpurea subsp. apollinea. These compounds possessed antioxidant and anticancer properties. The methanol extract showed antioxidant properties with DDPH and ABTS radical scavenging of 84% and 94%, respectively, relative to ascorbic acid and trolox. The anticancer effects of T. purpurea subsp. apollinea against the cancer cell lines MCF7 (IC50 = 102.8 ± 0.6 μg/mL), MG63 (IC50 = 118.3 ± 2.5 μg/mL), T47D (IC50 = 114.7 ± 1.0 μg/mL), HeLa (IC50 = 196.3 ± 2.3 μg/mL), and PC3 (IC50 = 117.7 ± 1.1 μg/mL) were greater than its anticancer effects against U379 (IC50 = 248.4 ± 7.5 μg/mL). However, it had no adverse effects on the normal cells (WI38) (IC50 = 242.9 ± 1.8 μg/mL). Therefore, the major active constituents presented in T. purpurea subsp. apollinea can be isolated and studied for their potential antioxidant and anticancer effects against breast, cervical, and prostate cancers and osteosarcoma.