This study examined the Core Mathematics assessment of the West African Senior School Certificate Examination (WASSCE) by the West African Examination Council (WAEC) in Ghana for "Depth of Knowledge and Context Characteristics" over a 20-year period. In all, 1245 assessment items were analysed. The results indicated that nearly 80% of the items assessed students' ability to either recall basic facts or perform straightforward routine procedures. In terms of the context characteristics, the results showed that about 70% of the items was framed within abstract context, with about 15% each framed within "semi-reality" and "real-life reference" contexts, respectively. Overall, the results indicated that the nature of the WASSCE Core Mathematics has not changed much over the 20-year period in terms of depth of knowledge and context characteristics. Implications of the results for teaching and learning of school mathematics, as well as recommendations for the Ministry of Education and WAEC, are provided.