In order to investigate the effect of fissure inclination on the mechanical properties, deformation, and crack evolution of the surrounding rock in the roadway, uniaxial compression experiments were conducted on sandstone-like materials with prefabricated fissures. The high-speed camera and DIC (digital image correlation) method were employed to analyze the strain distribution and the crack evolution of the specimen. The results demonstrated that the presence of fissures reduces the stress for crack initiation, with intact specimens producing new cracks from about 75% of peak strength and fissured specimens producing new cracks from 50% to 60% of peak strength. The fissure reduced the strength and elastic modulus of the specimen while increasing the strain. The fissure inclination of 45° exhibited the most significant changes compared to the intact specimen. The peak strength and elastic modulus decreased by 54.52% and 35.95%, respectively, and the strain increased by 151.42%. The intact specimen and specimen with 90° inclination are mainly distributed with the shear crack, tensile crack, and far-field crack, which are mainly tensile–tension damage; specimens with 0~75° inclination are mainly distributed with the wing crack, anti-wing crack, oblique secondary crack, and coplanar secondary crack, which are mainly shear slip damage. The direction of the extension of cracks is related to the fissure inclination. For specimens with 0° inclination, the new cracks mainly propagate in the direction perpendicular to the fissure; for specimens with 30° and 45° inclinations, the new cracks mainly propagate in the direction parallel and perpendicular to the fissure; for specimens with 60° and 75° inclinations, the new cracks propagate in the direction parallel to the fissure; and for specimens with 90° inclination, the new cracks propagate in the direction parallel to the fissure.