Mediterranean cropping systems, characterised by continuous cereal cropping, are largely dependent on synthetic inputs, such as N fertilisers. On the other hand, they face difficult pedoclimatic conditions, exacerbated by climate change. Diversification is seen as a way to increase cropping systems resilience. The aim of this study was to co-design diversified cropping systems based on the expertise of local stakeholders and co-assess their performance, using modelling data. Our case study is the Ebro valley in Spain, a Mediterranean area with great potential for diversification, particularly where irrigation is available. Two workshops were organized to i) define the reference system in the study area and its limitations ii) co-design diversified systems to overcome these limitations and iii) co-assess reference and diversified systems. Between the two workshops, the STICS soil-crop model was calibrated with local experimental data, enabling to simulate the inter-annual (2000–2021) agronomic and environmental performance of the reference and diversified systems. An economic analysis was conducted. Stakeholders evaluated all economic, agronomic and environmental aspects. The reference system was a continuous winter cereal crop based on synthetic N fertilisation and intensive tillage. The four diversified co-designed systems consisted in introducing pea and/or rapeseed every 2 or 4 years, reducing tillage and partially replacing synthetic N fertilisation with locally sourced livestock manure. Simulation results showed that wheat and barley grain yields remained stable with diversification. Pea and rapeseed yields were lower in rotations where both were introduced compared to when each was the only break crop over 4 years. At the system level, protein yield remained stable with diversification, however, energy yield decreased by 20 % when break crops were introduced twice and by 10 % when introduced once. Gross margins improved with diversification only when pea was introduced once (12 %), mainly due to reduced expenses (-31 %), while incomes remained stable compared to RCS. However, incomes decreased by 5 % when rapeseed was introduced once, and by 10 % when both break crops were introduced. Unexpectedly, environmental performance deteriorated with diversification, with increased N losses through ammonia volatilisation and nitrate leaching in the years following pea and rapeseed cropping, due to greater N availability in the soil. An increased use of pesticides was predicted by the stakeholders in diversified systems, where the environmental impacts were exacerbated with the higher presence of break crops. The reference system presented slightly lower N availability and increased soil organic carbon storage. Overall, the approach proved useful in identifying a diversification strategy that improved agronomic and economic performance, with the system including pea once every four years being the most efficient. However, the environmental trade-offs associated with the increased presence of pea and rapeseed in the crop rotation must be considered in order to mitigate the environmental risks.