This article describes a methodology and a four-step framework to measure and analyze competitive performance of the South African wine industry. Competitive performance is viewed as the ability to sustain trade against the competition in the global market. The economic sustainability of the South African wine industry is found to be highly dependent on its trading performance, with more than 40 percent of production consistently being exported since 2005. The views and opinions of South African wine executives through the Wine Executive Surveys of 2005 and 2008 are used to identify, describe and explain these competitiveness trends and to qualitatively comment on factors impacting on performance. The Porter Diamond is applied to derive the most important industry determinants of competitive performance. From this analysis changes in the “competitiveness space” of the South African wine industry are described and analyzed and a wine industry agenda is proposed to enhance competitive performance.