Damage to the remaining stand on steep terrain can be quite severe and is usually difficult to control during winching. Timber skidding, especially by agricultural tractor, is a common solution in small-scale forestry. One of the factors influencing remaining stand damage is winching on steep terrain, although, to date, this has only been studied in general. Limiting stand damage is possible when the factors causing the damage are well-known. Therefore, the aim of this paper was to study in detail the impact of slope steepness on different types of damage in the stand after winching, focusing in particular on: (1) the share of trees with damage (including natural regeneration), (2) the size of the wound, (3) the number of wounds per tree, (4) wound intensity, and (5) the position of the wound on a tree. Field observations were carried out in three beech (two in Italy and one in Iran) and two pine stands (in Italy), in which four classes of slope steepness were selected for each stand. After timber harvesting, damage to the remaining stand as well as to any natural regeneration was recorded. It was found that the share of wounded trees was directly related to slope steepness, although this was less obvious in the natural regeneration. On steeper slopes, there were larger wounds and, on average, there were more wounds per tree. Wound intensity also depended on the gradient of the slope. The size, understood as diameter at breast height, of the remaining trees on the slopes also had an impact on the wound characteristics: on thicker trees, bigger wounds were detected and a higher number of them. However, thicker trees were less often wounded. Wound position on a tree did not depend on slope steepness but it may have been related to stand density and size of winched timber.