Repeated mining is the main factor that leads to development, propagation, and eventual deformation of the overlying strata fissures in the steeply inclined and extra thick coal seams (SIETCS). The evolution of the overlying strata structure is closely related to microseismic events in a mine. As the mining depth increases, the evolution rules of the overlying strata structure become more complicated and can easily induce dynamic disaster accidents. To solve these problems, this paper established a physical similarity simulation model. Microseismic monitoring equipment was used to study the relationship between the evolution of the overlying strata structure and the energy-frequency of microseismic events. On the basis of the principle of quantitative seismology, the response relationship between the overlying strata structure and the microseisms at different mining stages was compared and analyzed from a quantitative perspective. The characteristics of cumulative apparent volume, energy index, and microseismic b value were used to reveal the precursor characteristics of overburden instability and failure. The results showed that due to the occurrence characteristics of coal seam, the distribution characteristics of rock stratum stress, and the effects of mining disturbances, the energy accumulation-release period after instability failure of the overlying strata induced by shallow mining was longer than the energy accumulation-release period induced by deep mining. And the deep coal and rock mass had a periodic “balance-instability-rebalance-instability again” dynamic evolution process under the disturbance of repeated mining. In the working face mining, the slope of the accumulative apparent volume ΣVA curve suddenly increased, and the energy index EI gradually decreased at the late peak period, which indicated the deformation and failure of overburden. However, the b value of the microseismic event presented the precursory characteristics of rock stratum fracture that gradually increased and then changed drastically.