We address the optimal allocation of stochastically dependent resource bundles to a set of simultaneous contests. For this purpose, we study a modification of the Colonel Blotto Game called the Tennis Coach Problem. We devise a thoroughly probabilistic method of payoff representation and fully characterize equilibria in this class of games. We further formalize the idea of strategic team training in a comparative static setting. The problem applies to several distinct economic interactions but seems most prevalent in team sports with individual matches, for instance, in Tennis and Sumo.