In recent years, a growing number of attachment-based studies have contributed to the understanding of both substance and behavioral addictions. Although gambling is a form of addictive behavior widespread all over the world, both among young people and adults, the evidence on the association between attachment-related phenomena and gambling has not yet been systematized in literature. The aim of the present study, therefore, is to provide a systematic literature review aimed at summarizing the empirical evidence on this topic. Following the updated 2020 PRISMA guidelines, a systematic search in four electronic scientific databases (Scopus, PubMed, PsycInfo and Web of Science) was conducted. After removing duplicates, 146 records were double-screened, with 12 articles meeting the inclusion criteria. Additionally, by means of a backward search a further article was selected. Altogether, 13 articles were selected for the present systematic review. With few exceptions, the results underline the significant role played by attachment-related phenomena in gambling behaviors, highlighting that specific attachment contexts have a different influence on gambling, also depending on whether gamblers are youths or adults. In particular, while secure attachment has proven to be a protective factor for the onset of gambling behavior, insecure attachment has emerged to be a vulnerability factor in two ways. On the one hand, it directly favors gambling behaviors; on the other, it affects coping strategies and the individual’s ability to identify and regulate emotions, which in turn predict gambling. Limitations, strengths, and implications of the present systematic review are discussed.