There is insufficient data regarding clinical characteristics, relapse rates, as well as lymph node metastasis of squamous cell carcinomas of the oral cavity (OSCC) developing from oral lichen planus (OLP-OSCC). The aim of this retrospective study was to evaluate clinical characteristics, as well as relapse, recurrence and survival rates of OLP-OSCC. In a retrospective monocenter analysis, all consecutive patients with an OSCC treated in the time period 1st January 2000-December 31 2016 were reviewed. All patients with OSCC developing from OLP/OLL (oral lichenoid lesions) were identified and analyzed for epidemiological data, risk profile, location of primary tumor, pTNM classification, lymph node metastasis, primary therapy, recurrence, and outcome. A total of 103 patients (45%♂/ 55%♀) with an average age of 62 ± 14year were included in this study. At the time of initial diagnosis, 17% (n = 18) of patients had cervical metastases (CM) whereas only 11% (11 patients) displayed advanced tumor sizes (T > 2). T-status (p = 0.003) and histopathological grading (p = 0.001) had an impact on the incidence of CM. 39.6% of the patients developed a relapse after an average of 24months with a mean of two recurrences per patient. Advanced tumor size had a significant impact on the 5year overall survival and was associated with disease-free survival of the patients (p < 0.001, respectively p = 0.004). Although initial lymph node metastases were not more frequent, more aggressive recurrence patterns compared to OSCC were seen for OLP-OSCC. Therefore, based on the study results, a modified recall for these patients is suggested.