Abstract: We study a Stackelberg model where two players compete in a sequential contest, and the player that successfully invests the most effort wins. Our formulation considers a probability that each player fails to invest their chosen level of effort, as captured by a failure function that increases with the amount of effort. The players each have their own cost of failure, as well as a maximum level of effort (capturing different abilities of the players). We prove three key results. First, we provide the optimal strategy for Player 1 (the follower), to maximize their utility given an observed effort exerted by Player 2 (the leader). Next, we characterize the optimal strategy to maximize the expected utility of Player 2, anticipating the optimal response by Player 1. Finally, we analyze the expected utilities of each player when both play their optimal strategy, and provide key insights into how heterogeneous player abilities and failure costs affect the outcomes of the game.