A method for characterization of penetration resistance of rubber compounds has been developed. The effects of properties of indenter, nature and dosage of fillers, and crosslinking density were investigated using the developed method. Indenter material was found to have negligible contribution to the penetration characteristics of the tire rubber compounds, whereas the indenter’s shape and size of the tip were important. A change in slope of the generalized penetration characteristic curve of the established quasi-static test was considered to be as the fracture initiation point. Penetration resistance has dependence on the elastic modulus and hardness of the compounds. Hysteresis losses of the compounds were also correlated with this permanent crack/fracture initiation depth and energy required to initiate the fracture. The carbon black filled samples have better penetration resistance than the silica filled vulcanizates. The effect of filler particle size on the penetration resistance was also demonstrated. Surface morphology of the specimens penetrated at different energy levels was examined using scanning electron microscopy. A theory on the forces acting at the tip of indenter while penetrating a rubber compound against a conical indenter has been proposed.