Started in 1991 in Madrid, the Middle East peace process has gathered three key actors of the Arab-Israeli conflict: Israel, the Palestinians and Syria. What lessons can be drawn from the process? Why did the talks fail to reach a comprehensive resolution of the Arab-Israeli conflict? The purpose of this study is to shed new light on the process that brought the Palestinians and Syria to negotiate with Israel, and compare their respective strategies, process and outcomes. Power asymmetry in favour of Israel has been a constant feature of the process, but the asymmetry was differently addressed by the Palestinians and the Syrians in their choice of strategies. The two tracks were also contrasted by Israel to extract additional concessions on the part of Palestinians. The role of power, in shaping strategies, perceptions and negotiation outcomes, is therefore evaluated. Core issues – borders, security, water, Jerusalem, refugees- are identified and construed against the background of the overall conflict between Israel and its neighbours over the West Bank, Gaza and the Golan Heights. The study draws on negotiation analysis and a conceptual framework is introduced to identify the parties’ strategies over twenty years, the impact of time on their respective bargaining positions, and explore possible links between actors, structure, process and outcomes. The research is based on primary and secondary sources, including official position papers, recently leaked confidential documents, interviews with key policymakers, first-hand accounts, and print media in English, Arabic and French. The underlying objective is also to assess the strongest party (Israel)’s strategy in the negotiations, and to question whether the objective was to maintain rather than challenge the existing status quo. The role of third-party mediation is evaluated, mainly in its nature (impartial/partial, facilitative/manipulative) and (in)effectiveness in bridging power asymmetry. The paper also evaluates the obstacles on the road to peace, and the potential for a resumption of wider peace talks for a comprehensive resolution of the Israeli-Arab conflict over land and water in the new regional context.