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Research suggests that linguistic features and cultural factors can play a role in test construction and influence how students interpret test items thereby creating assessment bias. This qualitative inquiry adopts a cross-disciplinary approach and uses measures of cultural responsiveness and language bias to assess standardized mathematics tests in the Secondary Entrance Assessment in Trinidad and Tobago. SEA tests from 2103-2018 generally showed cultural sensitivity in areas of gender and ethnicity. Some domains of activity referenced in word problems were within the experiences of primary school children; however, more heavily weighted questions reflected middle-class values and life experiences with vocabulary and contexts that might be unfamiliar to some test-takers. The implications for assessment are discussed and recommendations made.