Understanding the relationship between investments and firm performance has long been of interest to researchers. Studies regarding impact of information system/information technology (IS/IT) investments on firm performance so far report mostly mixed results which motivates the need for additional exploration on the issue. Similar type of inquiries is anyway under-represented in emerging markets like India. This study attempts to assess the impact of IS/IT investment made by Indian firms over the last one and half decades on their performance. Our proposed examination based on secondary data uses a combination of univariate and multivariate analysis to explore relative performance of investing firms in comparison to comparable firms not making an investment. The final results offer possibilities of both theoretical and practical contributions which are also delineated.