The year 1999 marked a watershed moment in the political history of Nigeria with the transition from military to civilian rule and the beginning of the Fourth Republic. Two decades later, the country has not only witnessed the longest period of civilian democratic rule but has also achieved a milestone with the alternation of power between the two dominant political parties. The augury, however, points to a democracy oscillating between consolidation and regression. This paper therefore interrogates two decades of democratisation in Nigeria in the context of the two main parties, the conduct of elections, and the level of representation of marginalised groups, particularly women. The paper contends that while it may be uncharitable to discount the incremental gains since the return to civil rule, the country is far from attaining the status of a consolidated democracy.