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This study examines how structural, linguistic, and contextual features of Ontario’s Grade 9 Education Quality and Accountability Office (EQAO) mathematics assessments affect the performance of multilingual students. Grounded in sociocultural and semiotic perspectives on mathematics learning, the research adopts a mixed-methods approach, combining qualitative content analysis of released test items with quantitative analysis. Findings highlight frequent occurrences of linguistic complexity, polysemous terms, multiple mathematical representations, and abstract contextual framing. The study proposes a replicable framework for analyzing assessment design and aims to inform instructional strategies that better support multilingual learners. Implications emphasize the need for more inclusive practices in both assessment and instruction, especially in Canada’s increasingly multilingual classrooms.