Peeling wheat yields higher-quality flour. During processing in a flaking machine, wheat kernels undergo continuous compression within the machine's chamber. As this compression persists, damage to the kernels intensifies and accumulates, eventually leading to kernel breakage. To study the damage characteristics of wheat kernels during peeling, this study established a continuous damage model based on Hertzian contact theory and continuous damage theory. The model's accuracy was validated through experiments, culminating in the calculation of critical parameters for wheat peeling. This study focused on different wheat varieties (Ningmai 22 and Jichun 1) and kernel sizes (the thicknesses of the small, medium, and large kernels were standardized as follows: Ningmai 22-2.67 ± 0.07 mm, 2.81 ± 0.07 mm, and 2.95 ± 0.07 mm; Jichun 1-2.98 ± 0.11 mm, 3.20 ± 0.11 mm, and 3.42 ± 0.11 mm). Continuous compression tests were conducted using a mass spectrometer, and critical damage parameters were analyzed and calculated by integrating the theoretical model with experimental data. The test results showed that the average maximum crushing force (Fc) for small, medium, and large-sized kernels of Ningmai 22 was 96.71 ± 2.27 N, 110.17 ± 2.68 N, and 128.41 ± 2.85 N, respectively. The average maximum crushing deformation (αc) was 0.65 ± 0.08 mm, 0.68 ± 0.13 mm, and 0.77 ± 0.17 mm, respectively. The average elastic-plastic critical pressure (Fs) was 50.21 N, 60.13 N, and 59.08 N, respectively, and the average critical values of elastic-plastic deformation (αs) were 0.37 mm, 0.38 mm, and 0.39 mm, respectively. For Jichun 1, the average maximum crushing force (Fc) for small-, medium-, and large-sized kernels was 113.34 ± 3.15 N, 125.28 ± 3.64 N, and 136.15 ± 3.29 N, respectively. The average maximum crushing deformation (αc) was 0.75 ± 0.11 mm, 0.83 ± 0.15 mm, and 0.88 ± 0.18 mm, respectively. The average elastic-plastic critical pressure (Fs) was 58.11 N, 64.17 N, and 85.05 N, respectively, and the average critical values of elastic-plastic deformation (αs) were 0.45 mm, 0.47 mm, and 0.52 mm, respectively. The test results indicated that during mechanical compression, if the deformation is less than αs, the continued application of the compression load will not result in kernel crushing. However, if the deformation exceeds αs, continued compression will lead to kernel crushing, with the required number of compressions decreasing as the deformation increases. If the deformation surpasses αc, a single compression load is sufficient to cause kernel crushing. Since smaller wheat kernels are more susceptible to breakage during processing, the peeling pressure (F) within the chamber should be controlled to remain below the average elastic-plastic critical pressure (Fs) of small-sized wheat kernels. Additionally, the kernel deformation (α) induced by the flow rate and loading in the chamber should be kept below the average elastic-plastic critical deformation (αs) of small-sized wheat kernels. This paper provides a theoretical foundation for the structural design and optimization of processing parameters for wheat peeling machines.