The acquired skill set prior to school entry has emerged as an important issue in research and policy internationally. Much evidence exists advocating the importance of early numeracy and literacy skills in later academic achievement and economic outcomes of students. The goal of this study was to determine the association between parents’ reports of engagement in pre-Grade 1 learning activities and school entry skills, and mathematics achievement in Grade 5. This study was based on empirical evidence using South African data from the 2015 Trends in International Mathematics and Science Study. These relationships were investigated by using stepwise multiple regression analysis. It was found that parent reports of engagement in pre-Grade 1 activities and acquired school entry skills are positively associated with student achievement at the Grade 5 level. This held even when taking other contextual home factors into account: socio-economic status and the frequency of speaking the language of the test at home. The role of the home is important in preparing children for school and has an impact on their later achievement. The home context should therefore be a key consideration in enhancing the South African education system. Parent reports are a good indicator of engagement in early learning activities and acquired numeracy and literacy skills prior to school entry.