The purpose of this study was to establish the risk factors for re-recurrences and disease-specific mortality (DSM) in recurrent thyroid cancer. Patients with recurrent thyroid cancer who underwent initial thyroid surgery from January 2000 to December 2019 at Seoul St. Mary's Hospital (Seoul, Korea) were assessed. Clinicopathological characteristics and long-term oncologic outcomes were compared between patients with one recurrence ( = 202) and patients with re-recurrences ( = 44). Logistic regression and cox-regression analyses were conducted to determine the risk factors for re-recurrences and DSM, respectively. Receiver-operating characteristic curve analysis was performed to determine the cutoff value for lymph node ratio (LNR) as a predictor of re-recurrences. DSM was significantly higher in the re-recurrence group compared with the single-recurrence group (6.8% vs. 0.5%, = 0.019). Surgical treatment at the first recurrence significantly lowered the risk of re-recurrences. Age (≥55), male sex, and LNR (≥0.15) were independent significant risk factors for re-recurrences in patients who underwent surgery at the first recurrence. Surgical resection is the optimal treatment for initial thyroid cancer recurrence. LNR at re-operation is more effective in predicting re-recurrence than the absolute number of metastatic LNs.