The National Curriculum Statement (NCS) for Mathematical Literacy (Maths Lit) states that the approach to Maths Lit teaching has to be contextualized – focusing on context-driven problems that relate to everyday lives. In this report I attempt to identify how teachers select and use context–oriented tasks for their grade 10 Mathematical Literacy classrooms. Data was gathered using a case study of four teachers, using interviews and analysis of various documents (work schedule and sample of learners‟ workbooks). Vygotsky‟s theory of mediation was used to analyze the findings in relation to the Maths Lit goals and principle of contextualization. The agendas from Graven and Venkat (2007) were used as the tool to analyze the tasks in the learners‟ books. A continuum based on these agendas was used as a descriptive tool of where teachers fit in relation to the context/content spectrum. The study concluded that teachers mainly used the work schedule and text books to select the context-oriented tasks for their learners. Teachers‟ selections of tasks were guided by the mathematical content to be taught. Most of the tasks‟ contexts lacked authenticity and the tasks consisted of pure mathematical content. The teachers mainly used the context to introduce the content to be learned. The tasks that were used promoted mathematical goals and were not context-driven. The level of authenticity promoted within the Maths Lit curriculum and its disseminated support documents such as work schedules, therefore needs to be investigated further.