In this study, taking the Sheng’an coal mine as an engineering background, the failure characteristics of the surrounding rock of a roadway under repeated mining in a close-distance coal seam is comprehensively illustrated through field measurements (e.g., drilling imaging), theory analysis and numerical simulation (finite difference method (FDM)). The results show that although the return airway 10905 remains intact, the apparent failure of the roadway’s roof and the coal pillar can be observed. In addition, the expression of floor failure depth caused by upper coal seam mining is obtained through elastic-plastic theory. Meanwhile, the deformation of the surrounding rock of the roadway increases with the increase of repeated mining times, especially for the horizontal displacement of the roadway on the coal pillar side. Moreover, the cracks’ evolution of surrounding rock in the roadway can be observed as asymmetric characteristics. Finally, the stability control technology of “asymmetric anchor net cable + I-steel” is proposed to prevent potential mining disasters, and the feasibility of this support scheme is verified by numerical simulation and field practices. It can meet the requirement of safe mining and provide guidelines to effectively solve the failure of a roadway in close-distance coal seam mining.