In order to study the difference of the roof caving structure and crack evolution between gob-side entry retaining and traditional coal pillar mining. Taking the 52605 and 52606 working faces of Daliuta Coal Mine as the engineering background.Through two groups of simulation experiments of similar materials. The mining process under two working conditions was simulated, recorded the process of overlying rock movement and fracture evolution. Research shows that, the crack rate formed at the end of primary mining is less than that of secondary mining when using gob-side entery retaining with flexible formwork concrete wall. But, after traditional coal pillar mining, the formation and evolution law of overlying rock fissures on both sides of coal pillar is similar. There are differences in crack rate, crack type, caving range and caving angle between the two coal mining methods. The crack rate of the overlying rock in the gob-side roadway retaining face of flexible formwork concrete wall is 5.0756%, the collapse range is within 50m, and the collapse inclination angle is in the range of 31°and86.9°. The crack rate of the overlying rock in the leaving coal pillar mining face is 2.8604%, the collapse range is within 40 m, and the collapse dip angle is between 50°and 52°, mainly the shear cracks developed along the caving dip angle. After the end of mining concrete wall in the face of gob-side entry retaining , the rock layer on both sides of the roof of the concrete wall does not slip, forming a hinged structure. On the other hand, after the mining is completed. the overlying rock layers on both sides of the coal pillar in the staying coal pillar mining face are cut off as a whole. The overlying strata form obvious structural differences on both sides of the concrete wall and coal pillar, which forms a significant concentrated stress effect on the load distribution of the concrete wall in the gob-side roadway retaining face.