The American Civil War is considered as one of the most famous written events in American historiography. Most Americans has a keen interest in studying this significant event than any historical milestones like the American Revolution (1774-1781), World War I (1914- 1918) and World War II (1939-1945), the achievements of American presidents (1789-present), and the Great Depression 1929-1939). However, American historians are still debating on important issues about the war, like the “real” causes that eventually triggered the war, the basis of citing Abraham Lincoln as the “greatest” American President who ever occupied the office and the factors that made the Union won over the Confederacy. While the conflict was long resolved, yet the war produced so many questions, answers and/or interpretation in contemporary times. On this note, the paper attempts to analyze some of the factors that contributed to the defeat of the Confederacy( Confederate States of America) against the Union (United States of America). The timeframe of this paper is focused on the American Civil War from 1861 to 1865. And lastly, the writer promised not to conceal biases in formulating this study.