Underground coal mining in coal-grain overlapped areas leads to land subsidence and deformation above the goaf, damaging cultivated land. Understanding the influencing process of coal mining on cultivated land and crops is important for carrying out timely land reclamation and stabilizing crop yield. Research has been carried out by using crop growth parameters to evaluate the damaging degree of cultivated land when the mining subsidence is stable, but few studies focus on the influence of land damage on crop growth when the subsidence is unstable during coal mining. Therefore, this study tracked the three growth stages of winter wheat by using UAV multispectral imagery to explore the dynamic influence of underground mining on winter wheat aboveground biomass (AGB). Firstly, a winter-wheat-AGB estimation model (R2 = 0.89, RMSE = 2.18 t/ha) was developed by using vegetation indexes (VIs), textures, and terrain data extracted from UAV imagery. Secondly, based on the winter-wheat-AGB estimation model, the winter wheat AGB was successfully estimated and mapped at different growth stages. The AGB of winter wheat in the coal mining-affected area was approximately 5.59 t/ha at the reviving stage, 8.2 t/ha at the jointing stage, and 15.6 t/ha at the flowering stage. Finally, combined with the progress of coal mining, the dynamic changing process of crops during underground mining can be inferred by analyzing the spatiotemporal variation in winter wheat AGB. Results showed that, in the dip direction, winter wheat AGB at the flowering stage was the highest at the compression zone, followed by the inner stretch zone, outer stretch zone, and neutral zone. The distance from the waterlogged area and the existence of cracks were found to be the important moderating variables affecting the crop growth status in the mining subsidence area. In the strike direction, there were significant differences in the wheat AGB-affected area as the mining proceeded. Even areas where AGB had previously significantly increased gradually transitioned to significant decreases with the end of mining. The research explores the dynamic changes in winter wheat AGB and land damage status during coal mining. It provides a rapid and non-destructive land-damage-monitoring method to protect cultivated land in mining areas.