Multi-factor coupling flight situations have the characteristics of strong dynamic complexity and always leading to "irreversible" chain reaction disasters. To research the modeling and simulation method of pilot-aircraft complex system in coupling flight situations, the impact of disadvantageous factors on flight safety is analyzed, and the factor coupling types are classified. Pilot-aircraft basic model is set up based on non-linear six-degree-of-freedom mathematical model and pilot manipulation model. Special researches are conducted on the modeling of pilot failure model. The delay time failure is defined and modeled, and reverse manipulation model is established. The robot pilot reliability model, sensor general malfunction model and overload sensor malfunction model are established. The subject of "automatic pull-up using robot pilot in the lowest permitted height" in GJB 626A-2006 is used for example, in which the "human-machine" and "machine - machine" disadvantageous factor double coupling situations are simulated and analyzed to verify the feasibility and practicability of the method.