Sustainable soil management practices, including conservation tillage practices, such as reduced tillage and no-till, are considered beneficial for different soil functions. So far, additional benefits of applying conservation tillage to improve crop yields under climate change are not fully clear and have rarely been investigated, particularly how potential benefits vary over time and under different pedo-climatic conditions. Using a cross-site and multi-model setup with four agro-hydrological models, this study sheds light on the questions whether, when, and where adaptation benefits of conservation tillage can be expected under future climate scenarios (time period 2020–2090, shared socio-economic pathways ssp2-4.5 and ssp5-8.5). To evaluate these questions, we used observations from three long-term experimental field trials in Denmark, Switzerland, and Austria to assess the benefits of no-till compared to conventional tillage regarding winter wheat (Triticum aestivum L.) productivity and soil hydrology, including key water balance components, such as actual evapotranspiration, percolation, and surface runoff. Our results suggest that the influence of climate scenarios of the respective sites overcome the potential benefits of the tillage management. While the simulated yields and water balance components showed different trends at the three sites, the intensity of the change was mainly driven by the climate models, where the climate model projecting the most intense changes in terms of temperature and precipitation most often also resulted in shorter growing periods and, related to that, higher yield losses. Therefore, no robust estimates of the adaptation benefits of no-till practices on winter wheat productivity could be quantified based on model ensemble projections, indicating stability in grain yields regardless of the tillage management. In general, the study results suggest that tillage as only adaptation measure is not sufficient to minimize future climate change-derived yield gaps and, consequently, ensure food security. Further work should explore the use of site-specific agricultural technologies, such as precision farming and variable rate application, as well as adaptation of (different) crops through targeted breeding for local conditions.