Gob-side entry retained with roadside filling (GER-RF) plays a key role in achieving coal mining without pillar and improving the coal resource recovery rate. Since there are few reports on the cyclic filling length of GER-RF, a method based on the stress difference method is proposed to determine the cyclic filling length of GER-RF. Firstly, a stability analysis mechanics model of the immediate roof above roadside filling area in GER was established, then the relationship between the roof stress distribution and the unsupported roof length was obtained by the stress difference method. According to the roof stability above roadside filling area based on the relationship between the roof stress and its tensile strength, the maximum unsupported roof length and rational cyclic filling length of GER-RF. Combined with the geological conditions of the 1103 thin coal seam working face of Heilong Coal Mine and the geological conditions of the 1301 thick coal seam working face of Licun Coal Mine, this suggested method was applied to determine that the rational cyclic filling lengths of GER-RF were 2.4 m and 3.2 m, respectively. Field trial tests show that the suggested method can effectively control the surrounding rock deformation along with rational road-in support and roadside support, and improve the filling and construction speed.