Pavement maintenance is widely thought to be critical for promoting their sustainability. It plays a pivotal role in sustainable and resilient transportation infrastructure for economic development and social inclusion improvement. Existing research mainly focuses on optimizing the maintenance strategies based on one player but ignores the inherent conflicts and complex interactions among multiplayer decision-makers. To address these issues, this research examined the problem of pavement maintenance involving the highway agency and maintenance service providers under the uncertainty of pavement conditions with the aim of optimizing maintenance strategies. A novel bilevel mathematical model was proposed to handle the inherent conflicts and complex interactions among decision-makers based on the Stackelberg game and Nash game. The goal is to obtain the Stackelberg–Nash equilibrium solution, where the highway agency, as the upper-level leader, determines the maintenance tasks, whereas the service providers, as the lower-level followers, provide the corresponding maintenance activities. To formulate this complex model, a bilevel particle swarm optimization (BLPSO) algorithm was developed for pavement maintenance. Finally, a practical case was used to demonstrate the practicality and efficiency of the proposed model. The results show that the mathematical model can provide feasible and effective pavement maintenance strategies for multiplayer decision-makers in real-world applications.