Providing simple information that identifies healthier/less healthy products at the point-of-sale has been increasingly recognized as a potential strategy for improving population diet. This review evaluated the effect on healthiness of food purchasing/intake of interventions that identify specific products as healthier/less healthy at the point-of-sale in food retail settings. Five databases were searched for peer-reviewed randomized controlled or quasi-experimental trials published 2000–2020. Effects on primary outcomes of the 26 eligible studies (322 stores and 19,002 participants) were positive (n = 14), promising (effective under certain conditions; n = 3), mixed (different effect across treatment arms/outcomes; n = 4), null (n = 3), negative (n = 1), or unclear (n = 1). Shelf-label studies (three studies of two rating systems across all products) were positive. Technology-delivered (mobile applications/podcast/kiosk) interventions were positive (n = 3/5) or promising/mixed (n = 2/5). In-store displays (n = 16) had mixed effectiveness. Interventions provided information on targeted healthier products only (n = 17), unhealthy products only (n = 1), both healthy and unhealthy (n = 2), and across all products (n = 5). No patterns were found between behavior change technique used and effectiveness. Study quality was mixed. These findings indicate that point-of-sale interventions identifying healthy/unhealthy options can lead to healthier customer purchasing behavior, particularly those delivered using shelf-labels or technology. Further research on discouraging unhealthy foods is needed.