Introduction The effects of postoperative early weight-bearing (WB) on walking ability, muscle mass, and sarcopenia have been investigated. Postoperative WB restriction is also reportedly associated with pneumonia and prolonged hospitalization; however, its effect on surgical failures has not been studied. This study aimed to assess whether WB restriction after surgery for trochanteric fracture of the femur (TFF) is useful in preventing surgical failure, considering the unstable fracture type, quality of intraoperative reduction, and tip-apex distance. Patients and Methods This retrospective analysis included 301 patients admitted to a single institution between January 2010 and December 2021, diagnosed with TFF, and who underwent femoral nail surgery. Eight patients were excluded, and finally 293 patients were included in the study. Propensity score (PS) matching yielded 123 cases; 41 patients in the non-WB (NWB) group and 82 patients in the WB group were included in the final analysis. The primary outcome was surgical failure (cutout, nonunion, osteonecrosis, and implant failure). The secondary outcomes were medical complications (pneumonia, urinary tract infection, stroke, and heart failure), change in walking ability, period of hospitalization, and sliding distance of the lag screw. Results Five surgical complications occurred in the NWB group and two in the WB group, with significantly more surgical complications in the NWB group ( P = .041). Cutout occurred in two cases, each in the NWB and WB groups. Two cases of nonunion and one case of implant failure occurred in the NWB group, but not in the WB group. Osteonecrosis did not occur in both groups. The secondary outcomes were not significantly different between the two groups. Conclusions The results of this retrospective cohort study using a PS matching approach showed that WB restriction after TFF surgery could not decrease the incidence of surgical failures.