Simple Summary Head and neck squamous cell carcinoma (HNSCC) is the neoplasm with the highest incidence in the head and neck regions. More than 350,000 new cases of carcinoma are diagnosed worldwide every year, but the prognosis has not improved significantly in the past few decades. In addition to smoking and alcohol habits, which represent the main risk factors for HNSCC, deregulation of non-coding RNAs have been identified as negative prognostic survival factors. The expression of miR-155 appears to be altered in many neoplasms and its different expression in tumor tissues can represent a prognostic biomarker of survival. By carrying out a systematic review and meta-analysis of the data in the current international literature, we aim to provide the most up-to-date data on the different expression miR-155 and to correlate those data with the prognostic indices of survival in HNSCC. Head and neck squamous cell carcinoma (HNSCC) is one of the most common cancers worldwide; in fact, it is among the top six neoplasms, with an incidence of about 370,000 new cases per year. The 5-year survival rate, despite chemotherapy, radiotherapy, and surgery for stages 3 and 4 of the disease, is low. MicroRNAs (miRNAs) are a large group of small single-stranded non-coding endogenous RNAs, approximately 18-25 nucleotides in length, that play a significant role in the post-transcriptional regulation of genes. Recent studies investigated the tissue expression of miR-155 as a prognostic biomarker of survival in HNSCC. The purpose of this systematic review is, therefore, to investigate and summarize the current findings in the literature concerning the potential prognostic expression of tissue miR-155 in patients with HNSCC. The revision was performed according to PRISMA indications: three databases (PubMed, Scopus, and the Cochrane Register) were consulted through the use of keywords relevant to the revision topic. Totally, eight studies were included and meta-analyzed. The main results report for the aggregate HR values of 1.40 for OS, 1.36 for DFS, and 1.09 for DPS. Finally, a trial sequencing analysis was also conducted to test the robustness of the proposed meta-analysis.