Southern Africa has experienced highs and lows in its efforts towards democratisation. Following political independence of Southern Africa states, the germination of democratisation was a rather slow process. A brief period of multi-party democracy introduced through pre-independence elections quickly dissipated and was replaced by one-party, one-person and, in some instances, military regimes. This era also coincided with the height of the Cold War globally and the heyday of apartheid in which inter-state conflicts had intensified. Since the late 1980s and early 1990s, a new dispensation has emerged wherein multi-party democracy has re-emerged in the context of the post-Cold War and post-apartheid dispensation, marked by relative peace dividend. However, democratisation in Southern Africa remains a mixed bag today. Some countries have not yet experienced the democratic transition. Others have managed to transition from one-party, one-person and military regimes to multi-party democracies. In various others, there are signs of reversal of democratic gains. This paper reviews the state of democratisation in Southern Africa with a view to understand why the regional record is so uneven across countries that form the Southern African Development Community (SADC). While the article presents a regional snapshot, it also presents comparative insights from Botswana and Lesotho.