The aim of the study was to evaluate the effectiveness of seagull-shaped nasolabial flap (NLF) along with adjunctive short-term oral pentoxifylline in the surgical reconstruction of oral sub mucous fibrosis (OSMF) following fibrotomy. We retrospectively evaluated 18 patients with grade IV oral sub mucous fibrosis treated by NLF. There were 3 females and 15 males. All patients were classified as stage IV OSMF with a mean preoperative mouth opening of 8.11±3.38mm. Postoperatively, patients were administered 400mg of pentoxifylline (PTX) thrice daily for 3 months. Patients were followed up at one month, six months and one year. Mouth opening, presence or absence of malignant transformation, relapse and complications were recorded at each follow-up. We found statistically significant increase in mouth opening from 8.11±3.3 to 37.67±3.74 in the postoperative period. The complications associated with NLF were very minimal. The PTX was well tolerated by all the patients. There was no incidence of relapse or rebound fibrosis seen in our series. To the best of our knowledge, this is the first time that oral pentoxifylline has been administered along with surgical treatment of oral submucous fibrosis to prevent relapse. The use of oral PTX as an adjunct along with surgical reconstruction in OSMF improves mouth opening, reduces burning sensation and relapse.