This dissertation applied the quantitative approach to the data gathered from online survey questionnaires regarding the three objects: Information Technology (IT) Portfolio Management, IT-Business Alignment, and IT Project Deliverables. By studying this data, this dissertation uncovered the underlying relationships that exist between the aforementioned objects. Furthermore, analyzing the data of attributes associated with these objects, this dissertation pinpointed the key factors used most to explain IT Project Deliverables, thereby offering practitioners a few practical means to improve IT Project Deliverables. The purpose of this study was to determine the degree to which IT Portfolio Management has an impact on IT-Business Alignment and to determine the degree to which this IT-Business Alignment has an impact on IT Project Deliverables. Consequently, this study was able to quantifiably depict the correlate coefficient, indicating how the practices of IT Portfolio Management influence the outcome of IT Project Deliverables. As a result, this dissertation claims that the enterprise that rigorously pursues the IT Portfolio Management ensures a higher degree of certainty for IT Project Deliverables. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]