Purpose: Unlike mucosal squamous cell carcinoma (SCC) in the head and neck, the role of elective neck dissection (END) against observation in clinically node negative (cN0) cutaneous SCC (cSCC) of the head and neck is not well elucidated. Retrospective reviews have not been able to delineate a relationship between survival outcomes and END. This review aims to answer if: In clinically node negative patients with advanced cutaneous SCC, does elective neck dissection, compared to observation, affect survival outcomes? Methodology: Systematic review from inception to 18th April 2024 of terms pertaining to “elective neck dissection”, “cutaneous squamous cell carcinoma”, and “head and neck” was performed. Three peer-reviewed databases (MEDLINE, Embase, Scopus), two clinical trial registries (Clinicaltrials.gov, ANZCTR), and grey literature were searched. Primary outcomes are overall survival, disease free survival, and disease free recurrence. Meta-analysis for occult metastatic rate was performed. This review was registered prospectively on PROSPERO (CRD42024537410). Results: Of 875 unique studies, 117 studies underwent full-text screening. Six studies underwent systematic review and meta-analysis. Of 522 patients included, 197 (37.7%) underwent END and 325 (62.3%) underwent observation. Six studies reported on overall survival, and four studies report on disease specific survival. There was no strong evidence for survival benefit. There is a possible benefit in disease-free survival. The occult metastatic rate estimated from the studies included in our systematic review and meta-analysis is 17.34% (95%CI 10.57 to 25.14). Studies were of low to moderate risk of bias. Conclusion: In advanced cSCC, END cannot be conclusively stated to improve overall or disease specific survival. There is potential benefit in improving disease free survival. The occult metastatic rate is below the recommended threshold for elective neck dissection.