The main objective of this study was to explore the origins and areas of the Amhara and Oromo political elite contestations in line with the possibilities and challenges of transforming their contestations into cooperative bargaining outcomes. In doing so, the study adopted a qualitative research approach with exploratory research design; and the data were collected from higher political elites of the six political parties from the Amhara and Oromo, namely; OPP, APP, NaMA, OLF, OFC, and ADFM. Besides, scholars from the IOS and ASC, as well as journalists of OBN and AMC were interviewed. Again, media discourses of elites and documents were also used. To collect primary data, a semi-structured interview was applied for purposively sampled key informants. The acquired data were analyzed through using political discourse analysis. Accordingly, the finding indicated that historiography over modern Ethiopian state-building; narrations fabricated externally and internally as well as the institutionalization of ethnic politics contributed to the origin of the Amhara and Oromo political elites’ contestations. These brought further contestation areas on the issue of revisiting the 1995 FDRE constitution and ethnic-federalism, claims over territory, and the issue of political representation for Amharas in ONRS. Nevertheless, political dialogue is being held between them since November 2017. However, the ongoing political dialogue is being challenged by the contending dream of the elites towards Ethiopia’s future, extremism, and populism as well as the weak political culture of bargaining. Due to this, the study comes up with political alternatives of changing the Amhara and Oromo political elite contestations into cooperative bargaining outcomes through applying deliberative democratic theory, elite bargaining, and consociational democratic-based power sharing. Key words: Amhara, Oromo, Political Elite, Elite Contest, and cooperative Bargaining