This study analyzes reasons for the successful of the Oakland Athletics in Major League Baseball as described in the bestseller, Moneyball. Benchmarking analysis is conducted to quantify the extent of Oakland’s achievement. The use of player performance analysis to develop a knowledge-based “David” strategy is investigated. The difficulties of applying the Moneyball approach in more complex invasion team sports are discussed. A hierarchical structural model of an invasion game is proposed as a conceptual framework and its application illustrated using data from English Premiership soccer. The technological, conceptual, and cultural barriers to the transferability of the Moneyball approach to other sports are assessed.