The growing interest in wood accessories has focused scientific research attention on wood cutting with small diameter tools. A problem that may arise when drilling wood is the phenomenon of wandering – when the hole is not made in the designed place. The difficulty in studying small diameter drill holes (0.5 mm to 0.9 mm) is due to the difficulty of automatic measurement. The development of an appropriate methodology may allow for the observation of this phenomenon without the need for high-class hardware and expensive software. This article presents the results of tests carried out on nearly 500 samples made of various wood-based materials (high-density fiberboard (HDF), medium-density fiberboard (MDF), chipboard, and plywood) in terms of the usefulness of the OpenCV computer vision library for the determination of wandering.