High-stakes placement testing at eleven plus remains a central and constant feature of education systems in the Anglophone Caribbean. In the Republic of Trinidad and Tobago, the Eleven Plus has been retained well into the era of universal secondary education, with a perceived legitimacy founded on the belief that examinations provide the fairest mechanism for allocating secondary school places. This study makes use of full cohort data from 1995 to 2005 to analyse Eleven Plus performance and placement outcomes for gender, geography, and assessment design changes. Data for the 279,904 students show that a 2001 assessment redesign led to larger gender differences in Language Arts and composite scores. For both the pre- and post-2001 assessment designs, placement within a first-choice school and assignment to a remedial track varied by geographic location, with variations larger after 2001. These patterns point to potential fairness issues within the placement system. (Contains 3 figures, 2 tables and 1 note.)