The short-lived polygamous moth Grapholita molesta (Busck) is an important fruit pest worldwide. Trapping males by synthetic female sex pheromones is not an effective reproductive control strategy. It is important to improve this technology by understanding the mating system of G. molesta. This study investigated mating opportunities and fertile egg production by altering the operational sex ratio, mating age, and male mating history in repeated single mating and multiple mating in the two sexes. Our results showed that the mating and reproductive parameters of virgin males were affected by the number and age of virgin females. Males preferred a female number ≤three-fifths of the male number or ≤2-day-old females, while they discriminated against a female number ≥three times of the male number or ≥5-day-old females. On the other hand, the mating and reproductive parameters of virgin females were affected by repeated single mating and especially multiple mating under different male mating histories. Females preferred once-mated males and discriminated against virgin males. These results indicated that mating systems including more and older virgin females for virgin males and different virgin males for virgin females may be suitable for suppressing G. molesta populations. Hence, these results revealed that preventing mating of virgin adults by synthetic female sex pheromones should be most effective in controlling G. molesta.