In order to reduce large deformation failure occurrences in non-pillar longwall mining entries due to roof weighting behaviors, a case study in Halagou coal mine was conducted on optimization and control techniques for entry stability in non-pillar longwall mining. The Universal Discrete Element Code (UDEC) modeling was adopted to study entry stability in non-pillar mining, and the characteristics of deformation and stress and crack propagation were revealed. The large deformation transmission between the entry-immediate roof and the gob-immediate roof could be eliminated by optimizing the entry roof structure through a directional roof-cutting method. The localized tensile stresses generated in the entry-surrounding rock caused the generation of coalescent macroscopic fractures, which resulted in the instability of the entry. The tensile stress state could be inhibited by an active flexible support system through enhancing the confining pressure on the surrounding rock. Serious rotation subsidence occurs in the entry roof due to periodic weighting of the main roof, which could be greatly reduced by a passive rigid support pattern. The numerical and field test results both showed that the roof weighting pressure was offloaded by the technique and that the deformation of the entry surrounding the rock in non-pillar mining was quite small. Thus, the technique can effectively ensure the stability of the gob-side entry, which can provide references for entry stability control in non-pillar longwall mining.