Moisture content has an important influence on the stratification and screening of materials on the surface of screens, and materials with different external moisture concentrations present different screening characteristics. A vibrating flip-flow screen (VFFS) is a two-body vibration system with a high-vibrating-strength screen surface developed based on a circular vibrating screen (CVS), which offers significant advantages in terms of handling sticky fine particles. To better understand the difference in screening performance between a VFFS and CVS under different external moisture concentrations, it is necessary to conduct a comparative study on the distribution characteristics of materials on the screen’s surface. In this paper, a CVS dynamic model considering the stiffness force and position of the damping spring is proposed, and the influence of different arrangements of damping springs on the amplitude and angular displacement of the screen is analyzed. Under different external moisture concentrations, the screening percentages of the 3–1 mm sized fractions in sections I–IV of a VFFS and a CVS are greater than those of 1–0 mm sized fractions. The screening efficiencies of CVSs and VFFSs are 92.54% and 92.19%, respectively, at an external moisture content of 4.30%, so the screening effect of a low-vibration-intensity screen surface is better in the case of better material stratification. When the external moisture content of the material was increased from 4.30% to 8.19%, the screening efficiency of the VFFS and the CVS decreased by 33.85% and 41.32%, respectively. The screening efficiency of the CVS is more sensitive to the external moisture content of a material.