The degradation of soil bonding, which can be described by the evolution of bond degradation variables, is essential in the constitutive modeling of cemented soils. A degradation variable with a value of 0/1.0 indicates that the applied stress is completely sustained by bonded particles/unbounded grains. The discrete element method (DEM) was used for cemented soils to analyze the bond degradation evolution and to evaluate the degradation variables at the contact scale. Numerical cemented soil samples with different bonding strengths were first prepared using an advanced contact model (CM). Constant stress ratio compression, one-dimensional compression, conventional triaxial tests (CTTs), and true triaxial tests (TTTs) were then implemented for the numerical samples. After that, the numerical results were adopted to investigate the evolution of the bond degradation variables BN and B0. In the triaxial tests, B0 evolves to be near to or larger than BN due to shearing, which indicates that shearing increases the bearing rate of bond contacts. Finally, an approximate stress-path-independent bond degradation variable Bσ was developed. The evolution of Bσ with the equivalent plastic strain can be effectively described by an exponential function and a hyperbolic function.