Objective: To identify or confirm any new or suggested independent histopathological predictors in Merkel cell carcinoma (MCC) of the head and neck (HN) correlated with outcome. Study design: Retrospective chart and pathology review. Methods: Between 1990-2010, 58 patients with HNMCC were identified for study. Pathologic specimens were reviewed and evaluated for independent prognostic factors and correlated with locoregional recurrence and disease specific survival. Results: The 2- and 5-year disease-specific survival (DSS) rates were 72.7%, and 63.6%, respectively. The local and regional recurrence rates were 12.0% and 24.1%, respectively. 25.9% of the patients developed distant metastases during follow-up. Tumor size (<1cm vs. >1cm) and the presence of a positive deep resection margin were independently found to be significantly associated with regional recurrence (p=0.01, and p=0.04, respectively). No other prognostic factors could be identified. Conclusion: Adjuvant radiotherapy cannot remediate a positive resection margin. Given these results consideration for revision surgery should be considered for a positive deep margin. Frozen section analysis may help to define the margins in this invasive and aggressive disease.