Impact fracture of single-crystal Si is critical to long-term reliability of electronic devices and solar cells for its wide use as components or substrates in semiconductor industry. Single-crystal Si is loaded along two different crystallographic directions with a split Hopkinson pressure bar integrated with an in situ x-ray imaging and diffraction system. Bulk stress histories are measured, simultaneously with x-ray phase contrast imaging (XPCI) and Laue diffraction. Damage evolution is quantified with grayscale maps from XPCI. Single-crystal Si exhibits pronounced anisotropy in fracture modes, and thus fracture strengths and damage evolution. For loading along [110] and viewing along [001] directions, (110) [110] cleavage is activated and induce horizontal primary cracks followed by perpendicular wing cracks. However, when loading along [011] and viewing along [111] directions, random nucleation and growth of shear and tensile-splitting crack networks lead to catastrophic failure of materials with no cleavage. The primarywing crack mode leads to a lower characteristic fracture strength due to predamage, but a more concentrated strength distribution, i.e., a higher Weibull modulus, compared to the second loading case. Moreover, the sequential primary cracking, wing cracking and wing-crack coalescence processes result in a gradual increase of damage with time, deviating from theoretical predictions. Particle size and aspect ratios of fragments are discussed with postmortem fragment analysis, which verifies fracture modes observed in XPCI.