We study a Stackelberg variant of the classical discrete-time Dynkin game, in which Player 1 (the leader) commits to a stopping strategy first and Player 2 (the follower) responds optimally. This leader-follower structure induces an optimal control problem for the leader and gives rise to intrinsic time-inconsistency. We first clarify notions of precommitment and equilibrium strategies in the Stackelberg setting, and contrast them with the Nash equilibrium in the standard Dynkin game using a finite-horizon example. We then consider an infinite-horizon framework with a time-homogeneous Markov process on a general Polish state space. We characterize the leader's value function under randomized precommitment strategies and show that randomized exact equilibrium strategies may fail to exist via a counterexample. Motivated by this nonexistence phenomenon, we introduce an entropy-regularized Stackelberg stopping game. The regularization induces a continuous response rule and yields the existence of randomized regular equilibria. We further show that these regular equilibria induce epsilon-equilibria for the original Stackelberg stopping game when the regularization parameter is sufficiently small. In the finite-state setting, we also establish a limiting result as the regularization parameter converges to zero.