In practical engineering, sand deposits or fills usually contain fines and are subjected to cyclic shear stresses induced by earthquakes, traffic, or waves which are superimposed on the initial static shear stress in natural or artificial slopes or beneath existing structures. To explore the combined and complex effect of an initial static shear stress and fines content of non-plastic silty sands on their deformation characteristics, pore pressure generation, and liquefaction susceptibility, the results of a comprehensive experimental program of cyclic simple shear (SS) tests are presented. Test conditions cover different fines contents fc (0-40%), initial void ratios e0, and initial static shear stress ratios (factor α=0-0.30). The observed types of failure are divided into four cyclic patterns: flow liquefaction, limited flow liquefaction, cyclic mobility, and plastic strain accumulation, depending on the initial state of the specimens and cyclic loading characteristics. Moreover, the threshold fines content (fthre), denoting the specific value of the fines content at which the behavioral properties of the mixture are reversed, is not affected by α level, and a practically unique value of around 24.5% is identified. The Kα values of sand-silt mixtures measured under cyclic simple shear loading would either increase or decrease with an increasing initial static shear level based on the initial global void ratio and fines content of mixtures; in particular, for a given initial global void ratio, the reduction of cyclic resistance due to the addition of non-plastic fines (fc < fthre) is much more pronounced as α increases. Finally, the larger the initial shear stress, the smaller the cyclic pore-water pressure (PWP) measured at failure. Therefore, a modified stress-based PWP generation model is proposed to predict the cyclic residual excess pore pressures developed under various initial static shear stress conditions in non-plastic silty sands in a satisfactory way.