While access to basic education is at the heart of development, the fact that sustained and meaningful education is critical for emancipation of the individual and entire society is no longer a matter of debate. Indeed, the myriad of advantages associated with sustained and quality mass education presuppose that it should be enjoyed by all as espoused in Education for All Goal 2 and Millennium Development Goals 2 and 3. Since Uganda was one of the first countries in Sub-Saharan Africa to introduce universal primary and secondary education in 1997 and 2007 respectively, this study endeavored to understand the extent to which the said democratization of education has eclipsed inequalities in accessing secondary schooling. This study largely used Uganda National Household Survey data for 2005/6 and 2009/10 that had information on schooling profiles of the household population and other characteristics that have been found to explain schooling outcome differentials. Through appropriate multivariate models, it was possible to map the evolution of inequalities in accessing secondary schooling for all children aged 13-24, making a transition for the ones that completed primary and accessing boarding facilities. Universalizing education at both levels has failed both to enhance completion of primary and dampen inequalities in accessing secondary schooling. Indeed, completion of primary and transition to secondary remain a prerogative of largely children from better socio-economic backgrounds, urban areas and the central region. Children in households below the 25th top percentile of household income, those in the rural, East, West and North, and those under household heads with less than secondary education, remain largely excluded from secondary schooling. Besides, whereas boarding schools (some of which are government schools) are known to offer better quality education that would enable social mobility for disadvantaged children, they are largely inaccessible to the poor as a matter of policy and this exacerbates inequalities in accessing quality secondary schooling. While inequalities in accessing secondary education for all eligible children have largely persisted, making a transition by children from poorer socio-economic backgrounds seems to be more difficult in the recent past than before implying that most children previously entangled in a vicious cycle of disadvantage, are most likely to remain so.