A cutting assembly for use with a stump cutting apparatus (8). Cutting assembly including a plurality of tool holders (14,16,18,20) and cutting tools (22,24,26,28) supported in said tool holders (14,16,18,20). The tool holders (14,16,18,20) placed in a side-by-side relationship on at least one side of the cutting wheel (10). Further, in an alternative example a single tool holder (200) supports multiple cutting tools (202).