Overburden strata fracture evolution is critical to dynamic disaster prevention and gas-relief drainage, so it is important to accurately determine the evolution relationships with mining disturbance. In this paper, experiments and numerical simulation were adopted jointly to characterize the time-varying fracture area of overlying strata. The experimental results showed that the roof strata gradually broke and collapsed with coal mining, which indicated the fractures of overburden strata developed in an upward direction. The fracture development causes were explained by numerical simulation, which showed that stress increase exceeded the strength of coal and rock strata, and fractures were formed and expanded. Both experiments and numerical simulation results showed the two sides and the top of fracture areas provided channels and spaces for gas migration and reservoir, respectively. In addition, the breaking angle of overburden strata and the height of fracture areas were analyzed quantitatively. Through microseismic monitoring at the mining site, the fracture scales and ranges of overburden strata were verified by the energy and frequency of microseismic events, which were consistent with the support of maximum resistance. The position of drainage boreholes was considered based on the results of overburden strata fracture evolution. Our study is aimed at promoting coal mining in safety and improving gas drainage with a sustainable approach.