The development of the Agri-Food sector in both the UK and EU is a government priority, especially in building more resilient and sustainable Agri-Food Supply Chains, which are also subject to a variety of local and global regulations, determined the Common Agricultural Policy or the World Trade Organisation. Understanding Agri-Food Supply Chains requires a detailed understanding of upstream and downstream relationships amongst suppliers and customers. However, considering the current regulation changes in EU, UK/EU Agri-Food decision-makers, are facing several market challenges, especially in adapting to the externalities they cannot control (technological innovation, new nutritional market demands, economy, political markets, food security and climate change). Based on the N8 SIMULAGRIT project, this research aims at identifying factors, both opportunities, and constraints, that currently influence Agri-Food Supply Chains performance once uncertainties in regulations are identified. Thus, and based on case studies from the UK, Spain, Italy, and Chile, a compressive AHP study of alternatives Agri-Food strategies to deal with such uncertainties has been carried out. From this, it is depicted that key criteria are in the context of Finance, Supply Chain and Logistics, Human Resources and National/International trade. Thus, the research work has helped to identify and evaluate a set of strategies which may be used to support further policy-making processes and scenarios