The deformation and failure law of stope roofs is more complicated than horizontal coal seams affected by the angle of the coal seam during the mining process of steeply dipping coal seams. This study focused on and analysed the working face of a 2130 coal mine with steep dipping and large mining height. Through the use of numerical calculation, theoretical analysis, physical similar material simulation experiments, and field monitoring, the distribution characteristics of roof stress, as well as the threedimensional caving migration and filling law, in large mining height working faces under the dip angle effect was investigated. The influence mechanism of the dip angle change on the roof stability of large mining heights was investigated. The results revealed that the roof stress was asymmetrically distributed along the inclination under the action of the dip angle, which resulted in roof deformation asymmetry. With the increase in the dip angle, the rolling and sliding characteristics of roof-broken rock blocks were more obvious. The length of the gangue support area increased, the unbalanced constraint effect of the filling gangue on the roof along the dip and strike was enhanced, and the height of the caving zone decreased. The stability of the roof in the lower inclined area of the working face was enhanced, the failure range of the roof migrated upward, and the damage degree of the roof in the middle and upper areas increased. Furthermore, cross-layer, large-scale, and asymmetric spatial ladder rock structures formed easily. The broken main roof formed an anti-dip pile structure, and sliding and deformation instability occurred, which resulted in impact pressure. This phenomenon resulted in the dumping and sliding of the support. The ‘support-surrounding rock’ system was prone to dynamic instability and caused disasters in the surrounding rock. The field measurement results verified the report and provided critical theoretical support for field engineering in practice.