Background: Locally advanced oral cancers are treated with a combination of surgery and chemoradiation. Definitive chemoradiation (Def CRT) or concurrent chemoradiation (CCRT) is employed only in rare instances when essential structures are at risk from unresectable tumors. The potential drawback of opting for radiation therapy upfront is the morbidity of surgery for residual tumors after Def CRT. Few centers have employed preoperative 50 Gy chemoradiation followed by surgery for resectable oral cancers. However, there is currently no well-established regimen for preoperative chemoradiation (50 Gy). We practice salvage surgery after Def CRT in our institution for some resectable locally advanced oral cancers due to patient, hospital, or logistical considerations. We found that there was considerable wound morbidity associated with these surgeries. With the knowledge that the preferred treatment approach for these patients would be surgery and adjuvant radiation, or Def CRT in a few patients, we decided to tread in-between the two standard treatment paradigms by treating such patients with preoperative chemoradiation (50 Gy) followed by surgery to reduce wound morbidity. We studied to compare the morbidity, functional (swallow) outcome, clinicopathological response pattern, locoregional recurrence, and disease-free survival between surgery following a definitive dose of chemoradiation (60–70 Gy) and 50 Gy chemoradiation. Materials and methods: A total of 62 patients of moderately advanced (T4a) oral cancer who underwent surgery for residue following radiotherapy (RT) between 2015 and 2021 were studied. The 50 Gy group consisted of 32 patients, and the conventional radiation group had 30 patients. The patients were followed up for the following outcome measures—wound morbidity, swallowing efficiency, postoperative histopathology, disease progression, locoregional recurrence, distant recurrence, and disease-free survival and death. Results: Wound morbidity was found to be lower in the 50 Gy preoperative radiation group compared to the conventional radiation group. We found no statistically significant difference in pathological response, swallowing outcomes, disease progression, recurrence, and disease-free survival. Conclusion: Operating on patients who were treated with 50 Gy was associated with less morbidity in comparison with the conventional dose (60–70 Gy). Since a significant percentage of patients after Def CRT require salvage surgery, the option of multimodality treatment with 50 Gy preoperative chemoradiation may be worth considering. This requires a standard assessment after completing 50 Gy to identify patients not responding to radiation. Large prospective trials are needed to arrive at a definite conclusion.