Infiltration is defined by the expression of the hydraulic conductivity of the soil, which we decided to monitor on an experimental field applying a modern system of land management (control traffic farming). The present study compared two different methods of monitoring the hydraulic conductivity of soil on a selected 16 ha plot of land in the suburbs of the village Kolíňany (Slovak Republic). During the growing seasons, crops such as oilseed rape, winter wheat, spring barley, winter barley, spring peas, and maize alternated in individual years. In addition to the study of hydraulic conductivity, a long-term experiment is underway to investigate the influence of technogenic factors on soil degradation using a system of controlled movement of machines in the field. A mini disk infiltrometer (method one) was used to evaluate the unsaturated hydraulic conductivity of the soil, and a double ring infiltrometer (method two) was used to measure the saturated hydraulic conductivity. Monitoring changes in soil infiltration capacity within the compacted and uncompacted lines required 26 monitoring points (20 for method one and 6 for method two). The first longitudinal line was compacted by an agricultural machinery chassis, and the second line remained uncompressed. The research also created transverse compacted lines at eight monitoring points (six for method one and two for method two). The results did not show a statistically significant difference when examining the effect of soil infiltration monitoring (compacted p = 0.123; uncompacted p = 0.99). When evaluating the statistical dependence on the compression caused by machinery in the track line, the hypothesis of significance was not confirmed (p = 0.12, at the level of 0.05). However, the results showed variability in the value of the difference factor between the two methods, ranging from 0 to 0.24. On average, it can be concluded that the results achieved using the double ring infiltrometer were 4.16 times higher than those measured with the mini disk infiltrometer. The variability of hydraulic conductivity was demonstrated not only in the compacted but also in the non-compacted part of the plot. In some places, the phenomenon of water repellency appeared, which could be caused by the drier location of the targeted plot.