One stump cutter cutting wheel disclosed herein includes a wheel structure having left and right sides and being rotatable about a central axis extending between the left and right sides. The left and right sides define receptacles having depths measured in an orientation extending along the axis. Cutter assemblies are mounted to the wheel structure and include cutters mounted to cutter holders. The cutter holders include base portions that fit within the receptacles, and the base portions each define at least one fastener opening. The base portions further define base thicknesses measured in the orientation extending along the axis. The receptacle depths are at least 0.25 times as large as the base thicknesses such that no more than 75 percent of the base thicknesses extend laterally outside the receptacles. Fasteners secure the cutter holders to the wheel structure and extend through the fastener openings defined by the base portions.