The soils in situ are subjected to various types of preloading histories. Extensive work has been devoted to understanding the impact of undrained preloading with different strain histories on the reliquefaction resistance of sands. This study primarily examines the effects of drained cyclic preloading histories on the liquefaction resistance of soils using DEM-clump modeling. The effects of preloading stress path and preloading deviatoric stress amplitude on the drained cyclic behavior and subsequent undrained liquefaction response are discussed. Moreover, the evolution of two microscale descriptors, including coordination number Z and fabric anisotropy degree ac, during the total process is analyzed. The results demonstrate that a smaller preloading stress amplitude and an increasing preloading cycle generally increase the liquefaction resistance of sandy soils. In comparison, a larger preloading stress amplitude significantly reduces the liquefaction resistance. We also reveal that drained cyclic preloading histories induce soil samples with different relative densities and fabrics. The relationship between relative density and liquefaction resistance of soils is not unique. Essentially, Z and ac are good indexes for determining the liquefaction resistance of soils with various drained cyclic preloading histories. The primary objective of this study is to elucidate the micromechanical effects of drained cyclic preloading on the liquefaction resistance of sandy soils.