In this study, a numerical simulation is used to study the effect of initiation methods on the damage distribution on both sides of an air-spaced charge blasthole using lead azide as the explosive and polymethyl methacrylate as the experimental material. The digital image correlation system determines the evolution of the global strain field and the strain attenuation pattern of the air section, and the dynamic caustics experimental system investigates the effect of detonation methods on the dynamic fracture behavior of the precrack. The experimental results show that the damage induced on both sides of the cylindrical charge blasthole has significant fractal properties. The damage degree corresponding to each initiation point of the charge section is the smallest, and the damage degree gradually increases along the detonation path. When it approaches the noninitiating end, the damage degree reduces further due to a decrease in the energy accumulation rate and a portion of the energy dissipation. When the outer detonation method is employed, both sides of the central air section are damaged, but not when the other detonation methods are used. The effect of different initiation methods on the radial compressive strain of the air segment strain field is mostly reflected in the strain size and strain decay rate, whereas the effect on the axial tensile strain is primarily reflected dynamically and in the decay rate. The attenuation coefficient of the strain field is the greatest when the outer detonation is initiated, regardless of whether the strain is radial or axial. The fracture behavior of the precrack end varies considerably depending on the detonation method. When both the inner and outer detonations are used, the crack exhibits a typical I type generated by tensile failure. When antarafacial detonation is used, the crack initiation is mixed I–II, and the specific performance is tensile-shear destruction. The origin of the crack initiation at the end of the precrack is described using LS-DYNA numerical simulation software, and the distribution pattern of the stress field at the blasthole wall is derived. The pressure distribution along the axial hole wall of the blasthole is considerably affected by different detonation methods. The charge section is mainly reflected in the position of the pressure peak and the pressure distribution shape, whereas the air section is primarily reflected in the size of the pressure peak and the pressure distribution shape.