Several studies suggested a negative association between olive oil (OO) consumption and the risk of several chronic diseases. However, an attempt to systematically search, organize, and evaluate the existing evidence on all health outcomes associated with OO consumption is lacking. The objective of this review is to describe the multiple health outcomes associated with OO consumption. The Medline, Scopus, and Web of Science databases were searched through 5 April 2024. The selected studies met all of the following criteria: (1) a meta-analysis of both observational (case-control and cohort studies) and interventional studies (trials), (2) an evaluation of the association between OO consumption, mortality, and/or the incidence of non-communicable/chronic degenerative diseases, and (3) a study population ≥18 years old. Two independent reviewers extracted the relevant data and assessed the risk of bias of individual studies. The PRISMA statement and guidelines for the Integration of Evidence from Multiple Meta-Analyses were followed. The literature search identified 723 articles. After selection, 31 articles were included in this umbrella review. The primary health benefits of OO were observed in cardiovascular diseases and risk factors, cancer, mortality, diabetes, and specific biomarkers related to anthropometric status and inflammation. As a key component of the Mediterranean diet, OO can be considered a healthy dietary choice for improving positive health outcomes.