<p>The wind oxidation zone has developed coal seams and overlying rock fractures, high rock porosity, strength attenuation, and poor self-stabilization ability, making it difficult to manage the roadway roof and extremely challenging to mine. Therefore, this paper investigates the variation characteristics of coal and rock samples in the wind oxidation zone of a specific mine through laboratory experiments, and elucidates the fracture development patterns of coal samples and rock masses in the same zone. Study on the deformation and failure characteristics of fractured surrounding rock in fully mechanized top coal caving faces in wind oxidation zones through borehole observation and macroscopic monitoring. Based on all the analyses, “deep hole-medium deep hole” coupling grouting reinforcement technology was proposed. The effectiveness of the grouting scheme was validated through a combination of numerical simulations and field engineering applications. These results show that the “deep hole-medium deep hole” coupling grouting reinforcement scheme could enhance the cohesion and bonding force of the coal sample and rock mass, improving the stability of the working face roof. These research results lay a foundation for safe mining of coal faces and provide a reference for safe and efficient production in coal mines under similar engineering conditions.</p>