Following the political changes of 1994 in South Africa, the decision was taken to replace the traditional skills-based education system at primary and secondary school level (Grades 1–12) with an outcomes-based education system (OBE). The implementation of the OBE system did not come without problems, giving rise to revised initiatives. The OBE approach, referred to as Curriculum 2005, was introduced into schools in 1998, for all learners in Grades 1- 6 and progressively phased in after that. In 2002, the OBE system was put on hold for the two upper grades of these learners. Learners in these two grades reverted back to skills-based learning for their last three years of schooling, i.e. in Grades 10 – 12. The most senior of these learners that had been subjected to four years of OBE and another three years of the old system finished their schooling in 2005 and 2006 and entered university in 2006 and 2007. These groups are of interest. Students ahead of them had their full schooling in the old system and students two years younger were only subjected to OBE. These students are the “group in the middle”. This paper reports on what the impact is of the growing pains of such a new, inadequately planned education system on the mathematics preparedness of students entering university. This report will be extended in 2009 when the learners that have been fully subjected to the OBE system enter university.