<p>Roof-cutting by dense boreholes has been applied in numerous mines in China, but research on its failure mechanism remains limited. To explore the fracture process of roadway roofs with dense boreholes, this paper conducts uniform load compression-shear failure experiments on rock samples with dense boreholes. A high-speed photography system recorded the complete crack propagation and penetration process between the holes. The influence of different drilling parameters on the failure of the rock samples was clarified. The results indicate that the fracture of rock samples with dense boreholes is a combination of tensile and shear failure. Compared to intact samples, dense boreholes significantly reduced the failure strength of the samples. The depth, inclination, diameter, and spacing of the drill holes, as well as the strength of the rock, all affect the crack propagation and strain distribution in the rock surrounding drill holes, thereby influencing the sample failure. The ranking of the impact of different drilling parameters on failure strength in ascending order is as follows: drilling angle, diameter, spacing, and depth. Hard rock exhibited a stronger resistance to failure compared to soft rock. The accuracy of the theoretical model of roof fracture by dense boreholes was verified by observing different failure modes in different rock sample types. These research results will provide a basis for future fundamental investigations and practical engineering applications of mine roof cutting using dense boreholes.</p>