Various factors have shaped relations between Libya and Egypt since Mu'ammar al-Qadhafi's advent to power in 1969. Differences in geo-strategic location, social and economic conditions, demographic processes, political structures and national resources, as well as contrasts in regional and international outlook, were substantial in generating bilateral conflict. On the other hand, a common denominator of religious and cultural identity and the supreme interest of both countries' regimes to combat the challenge posed by radical Islam, were significant in supporting rapprochement. Not surprising, therefore, were the oscillations in ties between tension and affinity. Notwithstanding the major effect of these factors on the moulding of bilateral relations, the impact of the personal leadership in each of the countries during this three-decade period should not be overlooked. The article examines, therefore, the role and effect of the wide scope of factors responsible for shaping the course of relations between Tripoli and Cairo, as well as their implications, which have transgressed the bilateral context, reaching the broader regional and international arenas.