Objectives/Hypothesis: Dysphagia is still a treatment-related morbidity, despite advances in treatment modalities for oral and oropharyngeal squamous cell carcinoma. This systematic review aimed to analyze the effects of swallowing outcomes of patients with oral or oropharyngeal squamous cell carcinoma treated with primary surgery with primary free flap reconstruction, with or without adjuvant therapy, for patients undergoing treatment with curative intent. Study Design: A comprehensive search strategy was undertaken across MEDLINE, CINAHL, Embase, and Scopus. Gray literature was sought through Cochrane Central Register of Controlled Trials, MedNar, and ProQuest. Methods: Studies included patients with oral cavity or oropharyngeal squamous cell carcinoma treated with primary surgery with primary free flap reconstruction. Swallowing function was the primary outcome, evaluated at 6 months or later following surgery. Methodological quality and data extraction was conducted as per the Joanna Briggs Institute Meta-Analysis of Statistics Assessment and Review Instrument and standardized data extraction tool. Results: Fifteen articles comprising eight cohort studies and seven case series were included. Postoperative radiotherapy and oropharyngeal resections were demonstrated to be associated with increased dysphagia. Conclusion: Advanced tumor-node-metastasis stage and use of adjuvant radiotherapy has been shown to have negative impacts on swallowing function. The majority of patients were able to have gastrostomy tubes removed at 6 months following curative therapy. Larger flap mass for the reconstruction of oral and oropharyngeal defects appeared to improve swallowing outcomes. A protocol for the identification of patients at high and low risk of developing dysphagia is proposed. Level of Evidence: N/A. Laryngoscope, 126:1572–1580, 2016.