As the United States is predicted to become the world’s largest wine consuming nation by 2008 with consumers purchasing across all price segments, one might assume that Californian wineries should thrive in this market. However, regulations and consolidation effects often prevent small wineries from being able to reach the U.S. consumer and they face similar problems with exporting. These wineries must seek specialty distributors that represent lesser-known brands, usually by attending trade shows at great expense. In turn, specialty distributors face the daunting challenge of finding wineries that best satisfy their portfolios’ needs. Given this problematic situation, can one provide assistance to these parties in their quest for finding appropriate partners? While this question no doubt has many positive answers, the approach we have chosen to explore is to develop a web-based matching program. We ask wineries and distributors to submit their respective attributes and their needs via a web questionnaire. Operations research methodology is then used to algorithmically determine the most promising partnerships, subject to mutual fit and based on constraints of supply, demand and avoidance of conflicting matches. We summarize the results obtained from the initial iteration of the program, a pre-qualification service created for the World Wine Market, a San Francisco trade show in 2004. We provide some of the participant feedback, including testimonials from parties that were successfully matched through the program. We also analyze the results to determine why the program did not recommend a greater number of matches and used this information and other feedback to assist in the development of the next program iteration While the conceptual contribution of our research is in providing the first documented application of “assignment problems” to model the optimal placement of wines into the distribution tier, this paper focuses instead on the potential practitioner contributions to the wine industry. A functional web based matching program could provide many small wineries with a means to expand their representation into additional markets domestically and internationally. Even if only a small fraction of the recommended matches take place, the business return from participation has enormous potential. We discuss the current improvements, which being funded through a Business and International Education Grant from the U.S. Department of Education. We conclude with ideas for future research, including extending this program to a broader range of participants.