Background: Surgical treatment is considered the best approach by many researchers for medication-related osteonecrosis of the jaws (MRONJ). While postoperative outcomes are mainly favorable, wound healing still fails in some cases. This retrospective study aimed to evaluate the factors affecting the postoperative healing of MRONJ. Methods: This study involved 400 osteoporosis patients who received surgical treatment from January 2009 to January 2018 in Kyungpook National University Hospital. The patient, drug, and clinical factors were collected as investigation variables. The obtained data were statistically analyzed to identify relationships between the factors and healing aspect. Results: Univariate logistic regression analysis showed that the route of drug administration, bone exposure, types of surgical management, and wound management had a significant influence (p < 0.05) on the healing outcome. Sequestrectomy with primary closure had a more positive effect on favorable healing. In the multivariate logistic regression test, the effect of wound management alone was not statistically significant (p > 0.05). Conclusion: In patients with osteoporosis, the factors such as intravenously administered drugs, fistulas that were probed to the bone, and surgical management with curettage were associated with a lower rate of postoperative complete healing of MRONJ, whereas primary closure of wounds led, possibly, to good healing outcomes. The strengths of the study include its relatively large sample size and that its results can hopefully aid in the clinical decisions for practitioners and future research studies for researchers.