IT systems are essential to the ongoing operations of organizations. Almost every industry prefers to use the standard applications that offers a whole range of features. For medium- and large-scale industries, SAP was the only alternative available in the 1990s, although Oracle and Microsoft Dynamics later entered the market. Benefits and cons of Microsoft Dynamics, Oracle, and SAP vary depending on the industry. The main purpose of this paper is to perform an in-depth critical analysis and comparison of IT enterprise resource planning applications. Which is conducted in the comparative analysis and discussion section of this paper. This paper focuses on the Functionality, benefits features & trends and drawbacks of a few IT ERP System Applications which are SAP, Oracle and Microsoft Dynamics respectively. It is their in-depth comparative analysis only after which an organization will be able to recommend or rather chose the right ERP System for their respective organization in the conclusion.  This paper has been divided into five sections which include Introduction, Literature Review, Comparative Analysis and Discussion, Recommendations and finally Conclusion.