Many species exhibit two discrete male morphs: fighters and sneakers. Fighters are large and possess weapons but may mature slowly. Sneakers are small and have no weapons but can sneak matings and may mature quickly to start mating earlier in life than fighters. However, how differences in competitive ability and life history interact to determine male morph coexistence has not yet been investigated within a single framework. Here we integrate demography and game theory into a two-sex population model to study the evolution of strategies that result in the coexistence of fighters and sneakers. We incorporate differences in maturation time between the morphs and use a mating-probability matrix analogous to the classic hawk-dove game. Using adaptive dynamics, we show that male dimorphism evolves more easily in our model than in classic game theory approaches. Our results also revealed an interaction between life-history differences and sneaker competitiveness, which shows that demography and competitive games should be treated as interlinked mechanisms to understand the evolution of male dimorphism. Applying our approach to empirical data on bulb mites (Rhizoglyphus robini), coho salmon (Oncorhynchus kisutch), and bullhorned dung beetles (Onthophagus taurus) indicates that observed occurrences of male dimorphism are in general agreement with model predictions.