This article investigates the benefits and supports provided by project management methodologies (PMMs) to project managers for the management and delivery of information technology/information system (IT/IS) projects. Using a qualitative approach, through case study strategy, the role of PMMs is examined in different business and project contexts. This article evaluates the benefit of PMMs based on their traits and characteristics and investigates PMMs in their operational context: where PMMs come from and how they support practitioners. The findings suggest a misalignment between the intended benefit of PMMs at the strategic level and the reported benefits by project managers at the project level. Additionally, it is shown that practitioners' expertise, accountability, and attitudes all have a direct influence on the extent to which PMMs contribute to and benefit the management of projects.