Surface water ponding and crop hampering due to soil wetness was monitored in order to evaluate the effects of conservation tillage practices and perennial grass cover on soil infiltrability for five years in situ in gently sloping clayey fields. Thirteen experimental areas, each having three experimental fields, were established in southern Finland. The fields belonged to: autumn mouldboard ploughing (AP), conservation tillage (CT) and perennial grass in the crop rotation (PG). In the third year, direct drilled (DD) fields were established in five areas. Excluding PG, mainly spring cereals were grown in the fields. Location and surface area of ponded water (in the spring and autumn) as well as hampered crop growth (during June−July) were determined in each field by using GPS devices and GIS programs. Surface water ponding or crop hampering occurred when the amount of rainfall was clearly greater than the long-term average. The mean of the relative area of the ponded surface water, indicating the risk of surface runoff, and hampered crop growth was larger in the CT fields than in the AP fields. The differences between means were, however, not statistically significant. Complementary soil physical measurements are required to investigate the reasons for the repeated surface water ponding.