Understanding prehistoric projectile weaponry performance is fundamental to unraveling past humans' survival and the evolution of technology. One important debate involves how deeply stone-tipped projectiles penetrate a target. Theoretically, all things being equal, projectiles with smaller tip cross-sectional geometries should penetrate deeper into a target than projectiles with larger tip cross-sectional geometries. Yet, previous experiments have both supported and questioned this theoretical premise. Here, under controlled conditions, we experimentally examine fourteen types of stone-tipped projectile each possessing a different cross-sectional geometry. Our results show that both tip cross-sectional area (TCSA) and tip cross-sectional perimeter (TCSP) exhibit a strong, significant inverse relationship with target penetration depth, although TCSP's relationship is stronger. We discuss why our experimental results support what is mathematically predicted while previous experiments have not. Our results are consistent with the hypothesis that when stone tip cross-sectional geometries become smaller over time in particular contexts, this evolution may be due to the selection of these attributes for increased penetration.