Soil stress imposed by tire-soil contact from transshipment vehicles used in mechanized sugarcane harvesting results in increase in the degree of compactness. In this study we aimed to: (i) estimate the magnitude and propagation of vertical stress into soil caused by sugarcane transshipment wheeling; and (ii) assess the risk and occurrence of soil compaction in an Oxisol of southeastern Brazil. Three tractor-trailers with a carrying capacity of 10, 21, and 30 Mg, and an autonomous truck-trailer with a carrying capacity of 20 Mg were evaluated as field traffic treatments. For each treatment, magnitude and distribution of vertical soil stress (σz) and soil strength (precompression stress, σp) were predicted by modeling estimation and risk of compaction was assessed by σp/σz relationship. The occurrence of soil compaction was evaluated based on measured changes in the bulk density and macroporosity (equivalent pore diameter > 50 μm) up to 0.70 m deep after wheeling. Estimates indicated that the autonomous truck applied stresses that reached 595 kPa at the soil surface beneath the centerline of the tire, imposing the greatest risk of compaction up to a depth of 0.35 m depth. The stresses at the soil surface beneath the centerline from the tractor-towed trailer tires ranged from 275 to 279 kPa, imposing a risk of compaction that did not exceed 0.29 m depth. All assessed transshipment configurations promoted soil compaction, detected by increases in the soil bulk density and decreases in the macroporosity, even at greater depths where risk prediction had not alerted to the soil compaction. The most significant impact on soil compaction was observed for the autonomous truck-trailer and the tractor-towed trailer with a carrying capacity of 30 Mg, also affecting subsoil, as evidenced by a relative increase in soil bulk density of 5 % and 7 % in the 0.30−0.50 m and 0.50−0.70 m layers, respectively, and a relative reduction in macroporosity of 40 % and 50 % in these same soil layers.