Studies on chip ejection from tools provide important information for the design of tools and effective chip collection elements used in woodworking machines. Among the chip properties, chip motion and its distribution are of particular interest for the design process. Until now, chip velocities have only been measured by manual tracking over a high-speed image sequence, which allows only a small scope of inspection. Here, we present the use of high-speed imaging in combination with particle tracking velocimetry as a new method for the semi-automatic evaluation of the magnitudes and directions of chip velocities. The methodology was tested in groove milling of particleboard. It was found that state-of-the-art particle tracking algorithms are suitable for quantitative analysis of chip motion in high-speed images. Therefore, spatial and temporal analysis of the chip velocity along the tool circumference are feasible and are presented here. In addition to chip velocity, chip collisions with the tool or other chips can be observed. This research also shows that image evaluation of chip sizes and shapes is potentially possible. In summary, the presented work provides methods that can quantitatively describe chip motion after chip formation. The experiments indicate that with each tooth engagement, new chips are formed, which initially move into the chip space at a median velocity higher than the cutting speed. After collisions with the tool and interparticle collisions, the particles leave the chip space of the tool at lower speeds. The machining tests performed with different process settings showed differences in the analysis results of chip movement. In the future, the presented methodology offers the possibility of investigating the relationships between tooth and chip space geometries, as well as different materials and the chip ejection of tools. Thus, the presented methodology provides a basis for creating a more general understanding of chip motion from machining operations, which can lead to innovations and improvements in chip collection.