The objective of this study was to evaluate long-term effects of two tillage regimes (ploughing and minimum tillage) on the bearing capacity of a clay rich soil, by using two different slurry tankers (4.1 and 6.6 Mg wheel load) and contrasting wheeling frequencies (1 and 10 passes). The soil strength was assessed by laboratory measurements of the precompression stress (Pc) at −6 kPa in topsoil (20 cm) and subsoil (40 and 60 cm) samples. Stress propagation, elastic and plastic deformation during wheeling were measured in the field with combined stress-state-transducer and displacement transducer system. Results presented in this study show that minimum tilled soil had 74% higher Pc than ploughed soil in the upper soil layer, whilst differences were less distinct in subsoil. Wheeling increased Pc at all soil depths. Compared to ploughing, higher strength in the upper layer of minimum tilled soil led on average to 60% and 48% reductions in the major principal stress with the use of the light and heavy slurry tanker, respectively. The extent of the major principal stress was dependent on the ground pressure in the topsoil. The first pass of a wheel caused the greatest damage in some cases, but all wheelings led to accumulative plastic deformation in both vertical and horizontal directions. Wheeling with high intensity would have exceeded Pc in all cases when soil was at a matric potential of −6 kPa. The results show that soil water content is an important factor influencing bearing capacity. Drier soil (−100 kPa), in combination with minimum tillage, limited the occurrence of stresses exceeding Pc in the upper soil layer.