Compared to the established, widely used and almost fully optimized cutting processes in woodworking, chipless cutting in the grain direction by means of shear cutting could offer several advantages. Therefore, a new chipless cutting process in the grain direction of wood is part of a current research project at the Institute of Natural Materials Technology of Dresden University of Technology. The process development should make it possible to produce a large-format work-piece contour reproducibly, in perfect quality and suitable for the material for the use as wooden flooring. The paper describes basically experimental tests of shear cutting of native wood in fiber direction. The tests involved several indigenous wood species in different moisture contents, different widths and thicknesses. In order to determine optimal processing parameters, the cutting angle, cutting edge position and cutting speed are varied. The primary evaluation criterions for grading the quality of the shear cutting process is an exact contour fidelity and a suitable edge quality for a homogeneous surface and a uniform appearance as a wooden floor. In addition to the visual evaluation, classic force–displacement diagrams were recorded and discussed. Apart from that large deviation of the fiber course as well as wood defects as large knots and resin inclusions lead to inadequate cutting quality.