Background: The purpose of this systematic review is to examine cooling intervention research in outdoor occupations, evaluate the effectiveness of such interventions, and offer recommendations for future studies. This review focuses on outdoor occupational studies conducted at worksites or simulated occupational tasks in climatic chambers. Methods: This systematic review was performed in accordance with Preferred Reporting Items for Systematic Reviews and Meta-Analysis (PRISMA) guidelines. PubMed, Embase, and Web of Science were searched to identify original research on intervention studies published in peer-reviewed journals that aimed at reducing heat stress or heat-related illness from January 2000 to August 2020. Results: A systematic search yielded a total of 1042 articles, of which 21 met the inclusion criteria. Occupations with cooling intervention studies included agriculture (n = 5), construction (n = 5), industrial workers (n = 4), and firefighters (n = 7). The studies focused on multiple types of cooling interventions cooling gear (vest, bandanas, cooling shirts, or head-cooling gel pack), enhanced heat dissipation clothing, forearm or lower body immersion in cold water, water dousing, ingestion of a crushed ice slush drink, electrolyte liquid hydration, and modified Occupational Safety and Health Administration recommendations of drinking water and resting in the shade. Conclusion: Current evidence indicates that using multiple cooling gears along with rest cycles may be the most effective method to reduce heat-related illness. Occupational heat-related illnesses and death may be mitigated by targeted cooling intervention and workplace controls among workers of vulnerable occupational groups and industries.