This paper systematically investigates the dynamic mechanical response and fragment characteristics of sandstone with asymmetrical conjugate fissures subjected to preexisting static stress based on the split Hopkinson pressure bar apparatus. The cross-fissured sandstone exhibits significant variations in mechanical behavior when exposed to higher dynamic strain rates under identical static pre-stress. The cross-fissured sandstone with a higher dynamic strain rate is characterized by a greater coupled strength under the same static pre-stress; for a given dynamic load, the highest coupled strength occurs under the static pre-stress of 60% UCS. The failure mode of the cross-fissured sandstone is predominantly governed by the dynamic strain rate, independent of static pre-stress variations considered in this investigation. At lower dynamic strain rates, the specimens typically exhibit a mixed tensile-shear failure mode, characterized by the dominance of larger fragments in the broken specimens. In contrast, under high dynamic impacts, the sandstone tends to fail in a shear-dominated manner, resulting in smaller fragments with a more uniform size distribution. Furthermore, the study explores how varying dynamic strain rates and static pre-stress influence the fragment characteristics of the cross-fissured sandstone. Higher dynamic strain rates and increased static pre-stress generally lead to smaller mean fragment sizes. This phenomenon is quantitatively described by fitting fragment size distributions using the Generalized Extreme Value (GEV) distribution, revealing a decrease in the location parameter (μ) and an increase in fractal dimension. These metrics indicate that higher dynamic strain rates and static pre-stress result in sandstone specimens breaking into smaller fragments with a more homogeneous size distribution. These findings contribute to a deeper understanding of rock dynamics, with potential implications for engineering applications involving similar geological configuration under dynamic loading conditions.