In this study, the change of microstructure, the formation of cracks, and the change of damage characteristics near the tip of a propagating crack in a highly filled elastomer containing hard particles embedded in a rubbery matrix were investigated using digital radiography X-ray techniques. Experimental findings reveal that the degree of inhomogeneity of the material's microstructure and the number of nonpropagating cracks increase as the applied strain is increased. Also, the damage characteristics near the crack tip are highly dependent on the loading history.