The objective of this study is to identify the incidence and characteristics of cases with positive margins on wide local excision for cutaneous melanoma of the head and neck (CMHN) and therefore provide a potential basis for selectively delaying reconstruction pending final histological clearance of melanoma. A systematic review of English language articles was performed on studies retrieved from PubMed and Web of Science. Original investigations published between July 1999 and June 2018 reporting on margin status of CMHN wide local excision specimens were included in the review. The incidence of positive margins after definitive resection for cutaneous melanoma in the literature ranges from 6 to 20.9%. The incidence is higher in cases of advanced patient age, diagnosis by shave biopsy, lentigo maligna melanoma subtype, desmoplastic subtype, tumor thickness, and ulceration. Delayed reconstruction remains the most oncologically sound decision, allowing for interpretation of margin status on paraffin-embedded tissue sections. However, resection and the resultant defect closure in a single stage is more expedient and potentially a more efficient use of resources. The risk–benefit ratio of immediate versus delayed reconstruction must be considered for each case. The incidence of positive margins is higher in cases of advanced patient age, diagnosis by shave biopsy, lentigo maligna melanoma subtype, desmoplastic subtype, increasing tumor thickness, and the presence of ulceration; delayed reconstruction should be strongly considered in these cases.