Background: Human papillomavirus (HPV) infection is the most common sexually transmitted viral infection in the world. HPV vaccination adherence rates in men are generally lower than in women. The aim of this systematic review and meta-analysis was to assess adherence to HPV vaccination in young working-age males (18–30 years old). Methods: A systematic review was performed using three databases: PubMed, Scopus, and Web of Science, according to the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA). Results: After duplicate removal, the initial search resulted in 478 eligible papers. With the exclusion of 425 papers after screening the abstracts, full texts of 53 articles were reviewed. Subsequently, 45 were excluded. Among the eight studies included, four (50%) examined the vaccination adherence in young adults through data registered in nationwide insurance or private companies’ databases, three (37.5%) in young adults in different settings through data collected from surveys and questionnaires, and one (12.5%) an HPV vaccination campaign in a family medicine residency practice. Conclusion: Adherence to HPV vaccination in men of working age (18–30 years) does not appear to be adequate (pooled prevalence 11%). In order to achieve a higher level of compliance, it is important to place an emphasis on vaccination campaigns in schools as well as in the workplace, after consultation with and approval from local, regional, and federal public health agencies.