The Catholic Missionaries in Ethiopia was encouraged since the beginning of the Portuguese assistance against the Muslims in the war of Ahmed Grañ. The successive Ethiopian monarchal authority was engaged to defend a full-scale war between the Muslim Sultanates of Adal, led by Ibin Ibrāhīm al-Ġāzī usually known by many writers as Ahmed Grañ. The Portuguese expansion with the succeeding Jesuit mission in Ethiopia was a turning point in the history of Ethiopia. Moreover, the Portuguese and Spanish Jesuit missionaries were more attracted by the strategic location of the country. This, in fact, enabled them to monitor the expansion of Islamic power in the Red Sea and the long experienced Christian faith in the country that had further consolidated the Ethiopian and Portuguese alliance. Initially, a Jesuit undertaking led by Father Andrés D. Oviedo first entered the country in 1557 to have started the top-down conversion process. This research aims to assess the opportunities and challenges of the Jesuits missionary strategy for the Catholicization of Ethiopia from top to down Approach. To achieve the objectives of this study, the researcher used qualitative research approach to investigate the issue and used historical research design for this study as well. Historical research requires access to the original events or records that took place in the past as distinct procedure for the investigation. Thus, the primary sources that were produced at the time under study as well as secondary sources were used. Primary data sources such as Royal chronicles, Tarike Nagast, Diaries of eye witness, Jesuit texts and European travel accounts by travelers who visited the northern part of the country by the time have been used. Published and unpublished secondary sources such as books, articles, journals and internet sources were utilized. More significantly, the researcher verified the authenticity and credibility of the acquired historical source through accuracy, occurrence, relevance and authority. The findings of the research revealed that the Jesuits missionary ambition to implant Catholicism remained in vain with bloody wars that claim thousands of human lives. Ultimately, the Jesuit missionaries expelled from the country. However, they left behind a theological controversy that gave it to local theme to Catholicism in Ethiopia that finally resulted in the doctrinal debate particularly centered on the teaching of the two natures of Christ. The intense doctrinal debate which was held during the seventeenth and eighteenth centuries Ethiopia hastens to the absence of strong centralized monarchial authority that eventually led to the era of the princes.