ABSTRACT - Understanding the impact of soil degradation on crop productivity is essential for decision-makers to predict agronomic, economic, and environmental outcomes of agricultural operations. Soil organic carbon (SOC) is influenced by the cropping system and affects soil health through its effect on other soil physical, chemical, and biological properties. Data from a 56-year long-term experiment in Uruguay's Pampa region were analyzed to quantify the effects of soil degradation on wheat (Triticum aestivum L.), and barley (Hordeum vulgare) yields. A significant degree of soil degradation was generated by six rotations with variable annual crop and pasture proportions (0%, 33%, 50%, and 66% of non hardvest pasture). Yield records (n = 368) and annual values of 14 explanatory variables containing soil, climatic, and management indicators were evaluated using random forest regressions. Rotation-induced SOC variation ranged from 1.2% to 2.6%, and robust relationships between SOC, soil physical, chemical, and biological properties were established. Over time, yields increased in crop pasture systems but plateaued for the annualized crop rotation (0% pasture). Yield improvements due to agronomic technology advances partly mask soil degradation effects. SOC losses lead to a reduction in yield, even when the SOC level was above 2%. Thus, no critical level of SOC could be determined. SOC interacted with climate indicators to impact yield. This analysis confirms the central role of SOC in yield outcomes beyond nutrient availability, and its potential to represent a wide range of soil functions. Our findings indicate that crop rotations with a higher percentage annual vs. perennial crops negatively impact SOC, associated soil properties, and yield potential. © 2021 The Authors