A successful path to purchasing negotiation often hinges on the buyer’s ability to gain relative bargaining strength. The buyer’s bargaining strength, in turn, depends upon the extent of the buyer’s preparation and preplanning for the negotiation. We postulate that the buyer’s level of expertise and/or simulated negotiation experiences through the experiential learning process help him/her better prepare for the negotiation and, thereby, increase his/her bargaining strength. Under such a premise, this study empirically investigates the impact of expertise and experiential learning on the bargaining position of purchasing professionals and their subsequent negotiation outcomes. The main objective of this chapter is to use both statistical data analysis and data mining techniques and demonstrate their usefulness in the optimal performance of business-to-business negotiations.