An approach for experimental solution of the problem of retrospective monitoring of changes in soil properties via comparative analysis of the results of soil studies performed in approximately the same place at different times is suggested. In essence, it is aimed at the step-by-step reduction of data uncertainty. First, the inaccuracy in georeferencing of an earlier studied soil pit is determined. Then, a key plot is thoroughly studied in order to determine the soil cover pattern in the area of the earlier studied soil pit. After this, the sampling pattern for the new study is chosen with due account for random and regular (predetermined) spatial variability in soil properties. We discuss the example of retrospective estimation of changes in the bulk density characteristics of a chernozem subjected to zoogenic turbation by earth burrowers in the Kamennaya Steppe area. After about 50 years, two parts of the soil profile have been subjected to compaction: the middle part of the plow horizon (10–20 cm), which has acquired a coarse blocky (cloddy) structure, and the soil layer disturbed by earth burrowers at a depth of 30–45 cm. In other parts of the modern soil profile, the bulk density characteristics remain in the same range as those determined 50 years ago.