The purpose of this study is to analyze the fracture resistance of reattached tooth according to the resin materials and tooth preparation type under physiological conditions. Uncomplicated crown fracture in the oblique direction was reproduced on the extracted 64 anterior teeth. Depending on the composite resin material, reattachment was performed using a flowable resin and a packable resin. Depending on retentive forms, reattachment was performed using simple reattachment, 1.0 mm × 1.0 mm labial chamfer bevel, 1.0 mm × 1.0 mm lingual chamfer bevel and 1.0 mm × 1.0 mm circumferential bevel. A load was applied to the palatal surface of the tooth using a universal testing machine at an angle of 125 degree, which is the interincisal angle of normal children. Under the masticatory pressure condition, fracture resistance of lingual chamfer groups was 28.28 ± 7.41 MPa and 27.54 ± 4.45 MPa, which was significantly higher than those of simple reattachment groups, 17.21 ± 5.87 MPa and 20.10 ± 6.00 MPa, in both flowable and packable resin groups. When considering the lingual force similar to masticatory pressure, the fragment retention was significantly improved when the lingual chamfer was formed compared to the simple reattachment. Clinicians may consider the design of the lingual chamfer in order to improve fracture resistance to masticatory pressure during fragment reattachment.