With the rise of financial technology (Fintech), businesses are increasingly adopting Cashless Payment Systems (CPS) to enhance transaction efficiency and effectiveness. This study compares the factors influencing retailers’ adoption of CPS in Sweden and South Africa, analyzing both similarities and differences across these distinct contexts. Using an interpretive comparative analysis approach, the study applies qualitative thematic analysis to 28 semi-structured interviews conducted with retailers from both countries. From the analysis, we generated 5 key themes: cost implications and financial challenges, convenience and efficiency, regulatory compliance and standards, trust and security perceptions, and infrastructure and accessibility. The findings indicate that context-specific environments shape retailers’ CPS adoption decisions. To the best of the authors’ knowledge, this is the first study to compare CPS adoption among retailers in Sweden and South Africa. The study provides valuable insights for policymakers, regulators, payment service providers, and other stakeholders seeking to promote CPS adoption among retailers. It highlights the need for a multi-faceted approach and context-appropriate interventions to support this cashless transition effectively, from retailers’ perspective.