TiB-whisker-reinforced TiBw/TC4 composites are widely used in aviation, aerospace, automotive, and various other industries. However, the drilling force and temperature have a large effect on the drilling micromechanical properties of TiBw/TC4 composites. In order to explore the micro-mechanical properties and promote the optimization of drilling process, the representative volume elements of TiB_W/TC4 composites were established in the Digimat-FE software tool to determine the micromechanical properties and failure mechanism of TiBW/TC4 composites. The results show: (1) maximum stress occurs at the whiskers, whereas the minimum stress appears within the basket matrix region of the reinforced phase. (2) When the force reached 300 N and the temperature reached 75 °C, the junction between the whiskers and the matrix firstly failed; when the force reached 525 N and the temperature reached 112 °C, the matrix began to fail; when the force reached 675 N and the temperature reached 138 °C, the whiskers failed. (3) The main reason for the failure of the junction between the matrix and the whiskers was that the shear stress exceeded the connection strength and the axial stress accelerated the failure process. Displacement and rotation of the whiskers were shown to occur at the moment of junction failure, owing to differences in the stress experienced on different sides of the material.