For testing how cover crops and different fertilization managements affect the soil physical properties in a plough based tillage system, a five-year crop rotation experiment (field pea, white potato, common barley undersown with red clover, red clover, and winter wheat) was set. The rotation was managed under four different farming systems: two conventional: with and without mineral fertilizers and two organic, both with winter cover crops (later ploughed and used as green manure) and one where cattle manure was added yearly. The measurements conducted were penetration resistance, soil water content, porosity, water permeability, and organic carbon. Yearly variations were linked to the number of tillage operations, and a cumulative effect of soil organic carbon in the soil as a result of the different fertilization amendments, organic or mineral. All the systems showed similar tendencies along the three years of study and differences were only found between the control and the other systems. Mineral fertilizers enhanced the overall physical soil conditions due to the higher yield in the system. In the organic systems, cover crops and cattle manure did not have a significant effect on soil physical properties in comparison with the conventional ones, which were kept bare during the winter period. The extra organic matter boosted the positive effect of crop rotation, but the higher number of tillage operations in both organic systems counteracted this effect to a greater or lesser extent.