The study of the water entry of successively fired projectiles under a wave environment is of great significance for the development and application of supercavitation weapons. In this paper, the supercavitating flow field of two successively fired projectiles entering water under different wave conditions is numerically simulated by the volume of the fraction model considering the cavitation of water. The motion of projectiles is handled by the overlapping grid technology and the simulated projectiles have six degrees of freedom. The effects of different wave phases and wave heights on the supercavitating flow field and the dynamic loads of the projectiles are studied. The research results show that the wave phase has an effect on the evolution and size of the supercavitation and the effect of the wave phase on the water splash above the free surface is more obvious. The peak of the drag force of the first projectile under conditions of different wave phases with 0.12 m wave height can be reduced by about 50% compared with that under the no-wave condition. The wave phases have an effect on the peak of the drag coefficient, and for the first projectile the peak under the condition of the 180° phase is about 40% lower than that of the 0° phase. The peak of the drag coefficient of the first projectile decreases with the increase in wave height. When the wave height increases from 0.0 m to 0.05 m, the peak value decreases by about 45%. For all conditions, regardless of wave phases or wave heights, the peak of the drag coefficient of the second projectile is obviously much lower than that of the first projectile. Accordingly, the decrease in the velocity of the second projectile is far slower than that of the first one. Negative values of the drag coefficient on the second projectile are observed when the second projectile enters the cavity of the first one.