There is an enduring discussion in the literature on why African opposition parties often fail to unite to fight the incumbent from a position of strength. Much of the extant studies have examined success stories of pre-electoral coalition-building in established democracies. There is less focus on why African opposition parties fail to form coalitions. In seeking to contribute to this debate, the article examines why Zimbabwean opposition parties failed to coalesce to form a pre-electoral coalition ahead of the 2018 election. This is against the axiom in the literature that pre-electoral coalitions do matter in increasing opposition stakes in elections, as read in line with the historical context of countries like Kenya. Using evidence gleaned from a qualitative study, it is argued that opposition-led pre-electoral coalitions remain uneasy to establish, especially in competitive authoritarian regimes like Zimbabwe, owing to structural and co-ordination challenges.