Conventional hydraulic fracturing has several disadvantages, including a short effective extraction time and low fracture conductivity during long-term extraction. Aiming at overcoming these shortcomings, a similar simulation test of repeated hydraulic fracturing was conducted in this study, and the evolutionary rules regarding the injection water pressure and stress distribution of the coal seam roof during this repeated hydraulic fracturing were revealed. The research results show that after multiple hydraulic fracturing, the number of cracks in the coal seam and the range of fracturing influence have increased significantly. As the number of fracturing increases, the initial pressure required for cracking decreases. The highest water injection pressure of the first fracturing was 2.8 MPa, while the highest water injection pressures of the second and third fracturing were 2.7 MPa and 2.4 MPa, respectively. As the number of fracturing increases, the area of increased stress will continue to expand. After the first fracturing, the impact radius of fracturing is 100 cm. After the second fracturing, the radius of influence of fracturing expanded to 150 cm. When the third fracturing was over, the radius of influence of the fracturing expanded to approximately 250 cm. It can be seen that, compared with conventional hydraulic fracturing, repeated hydraulic fracturing shows better fracturing effect. The research results can be used as a basis for repeated hydraulic fracturing field tests to increase coal seam permeability.