Assessing the effect of the timing and sequencing of various policy regimes on optimizing agent behavior is both important and difficult. To offer some insights, this article examines a timing decision from sports. The penalty shootout in football (soccer) has long been seen as problematic, among other reasons because it creates incentives for excessively cautious play during extra time. One proposal to alleviate this has been to alter the timing, and stage the shootout before (rather than after) extra time with the result binding only if the subsequent extra time offers no resolution. Carrillo’s (2007) theoretical model shows that since the effect of this rule change is ambiguous in theory, the proposal’s desirability needs to be assessed empirically. Using a comprehensive match data set, the authors compare scoring outcomes of various treatment and control groups, whereby the former simulate closely players' incentives from the proposed rule change, and the latter represent the current timing. Most importantly, the authors examine how extra time scoring probabilities depend on a goal being scored in the first 5 (or 15) min of extra time. Their estimates suggest that bringing the shootout before extra time would substantially alter the players' incentives in extra time and produce more overall attacking play. Quantitatively, the rule change is predicted to increase the odds of extra time scoring about threefold. Specifically, for the FIFA World Cup and the UEFA club competitions, the probability of scoring in extra time is estimated to increase on average by 45–60%, depending on various factors such as the result in regulation time, balancedness of the teams, and home ground advantage. In summary, all these results suggest that the case for trialing the proposed rule is strong. More generally, they highlight the incentive channels through which sequencing of policies may determine their effectiveness.