The base drag is a critical component of the overall drag experienced by projectiles which arises due to the low-pressure wake formed behind the projectile as it moves through the air. Base bleed, boat tail, and other active and passive ways are utilized to decrease this component of drag and increase performance and range. This study focuses into how incorporating bleed holes of various types can affect the drag characteristics at the base, of the projectile. Computational fluid dynamics (CFD) simulations were carried out using the CFD++ solver to analyze the flow behavior and drag forces. Three parameters—holes entry and exit locations, entry angle—were methodically varied in the study to evaluate their impact on the base pressure and total drag of the projectile in supersonic flow at Mach 2. For some design iterations, where there was an appreciable amount of drag reduction at Mach 2, numerical analysis was also carried out for other Mach Nos. such as Mach 0.6, 0.8, 1, 1.2, 1.5, and 2.5. Comparison was also done on the effect of bleed holes with and without the presence of a rotating band. Through visualizations of contour plots and analysis of extracted data, it was evident that each parameter impacts the base drag in a different way and also has an effect on the near-wake flow which will be discussed in this paper. The reduction in base drag was found to be greater when the bleed holes exited through the base lip rather than into the cavity. In the subsonic regime, the base drag reduction was up to 16%, while the total drag reduction was up to 5% in the geometry with bleed holes exiting through the base lip. This underscores the importance of optimizing bleed holes design for aerodynamic efficiency in projectiles.