Complex food retail settings, where multiple food retail outlets operate in close proximity are common. Despite their ubiquity, there remains a significant knowledge gap regarding healthy food retail interventions implemented within these settings. Furthermore, understanding the factors affecting the implementation of interventions in these settings remains limited. This systematic review aimed to (1) identify and describe complex food retail settings where interventions were implemented to promote the healthiness of foods purchased, (2) synthesise the evidence on the effectiveness of the interventions implemented, and (3) identify enablers and barriers to the implementation of the interventions in these settings. Four databases, namely, MEDLINE Complete, Global Health, Embase, and Business Source Complete, were searched until December 2022. The Effective Public Health Practice Project quality assessment tool was used. Six studies reported on the implementation of interventions promoting healthy food purchases across multiple food retail outlets. Three studies each described two complex food retail settings: university and hospital. Interventions including promotion and promotion plus price improved the healthiness of foods purchased. There was limited description of institutional food policies, conceptual frameworks, formative research, or evaluation outcomes to inform the implementation of interventions in these settings. No study analysed enablers and barriers to the implementation of interventions. No study identified their settings as complex food retail settings. There is limited evidence describing complex food retail settings, their impact on intervention effectiveness, and associated enablers or barriers. Investigating factors influencing the effectiveness of interventions implemented within complex food retail settings is critical to support their implementation at scale.