This paper investigates repeated win-lose coordination games (WLC-games). We analyse which protocols are optimal for these games, covering both the worst case and average case scenarios, i,e., optimizing the guaranteed and expected coordination times. We begin by analysing Choice Matching Games (CM-games) which are a simple yet fundamental type of WLC-games, where the goal of the players is to pick the same choice from a finite set of initially indistinguishable choices. We give a fully complete classification of optimal expected and guaranteed coordination times in two-player CM-games and show that the corresponding optimal protocols are unique in every case - except in the CM-game with four choices, which we analyse separately. Our results on CM-games are essential for proving a more general result on the difficulty of all WLC-games: we provide a complete analysis of least upper bounds for optimal expected coordination times in all two-player WLC-games as a function of game size. We also show that CM-games can be seen as the most difficult games among all two-player WLC-games, as they turn out to have the greatest optimal expected coordination times.