In the present work, we studied the effect of the growing region (IV, Metropolitan or VI - VII regions), quality classification (“Varietal”, “Reserva”, and “Gran Reserva”) and harvest year (2000-2012) on the total phenolic content and antioxidant capacity of thirty-six Chilean Cabernet Sauvignon red wine samples. The Folin-Ciocalteu (FC) and (Oxygen Radical Absorbance Capacity) ORAC methods, employing fluorescein and pyrogallol red as probes, were applied to establish the properties of the wine samples. The obtained results show a strong dependence at of the three indexes on the grape growing region, with higher values obtained in wines from the IV region. These results can be related to the climatic characteristics of this Region, which include dry weather and large temperature differences (nearly 20 °C) between day and night.