Indian organised retail industry is poised for growth. Rapid state of change due to speedy technological developments, changing competitive positions, varying consumer behaviour as well as their expectations and liberalized regulatory environment is being observed in organized retailing. Information is crucial to plan and control profitable retail businesses and it can be an important source of competitive advantage so long as it is affordable and readily available. DSS (Decision Support Systems) which provide timely and accurate information can be viewed as an integrated entity providing management with the tools and information to assist their decision making. The study, exploratory in nature plans to adopt a case study approach to understand practices of organized retailers in grocery sector regarding applications of various DSS tools. Conceptual overview of DSS is undertaken by reviewing the literature. The study attempts to describe practices and usage of DSS in operational decisions in grocery sector and managerial issues in design and implementation of DSS. Comparision across national chain and local organized retailer in grocery sector reveals that national chain having implemented ERP partially are mostly using the same for majority of operational decisions like inventory management, CRM, campaign management. Two local players use spread sheets and in house software to make the above operational decisions. The benefits realized remain the same across the retailers. Prioritization as well as quantification of benefits was not communicated. The issues of coordination, integration with other systems in case of ERP usage, training were highlighted. Future outlook of DSS by the respondents portrayed a promising picture.