The number of students completing mathematics education at higher levels are in decreasing numbers, despite good grades at primary level. This research study sought to explore the mathematics learning trajectory by collecting Mathematics grades obtained by 1652 students at the end of primary and secondary schooling. Data analysis showed a moderate association between these grades. But those who performed well at the primary level did not necessarily study the subject at the same learning performance at higher levels. This research study unveiled that girls, in general, tend to maintain their learning performance better than boys at higher levels. It also revealed that some students experienced a positive turning point in their learning, and the overarching conclusions from students’ interviews included perceived usefulness of Mathematics education, intrinsic and extrinsic motivation to boost the learning process and the need to overcome past hurdles. Finally, a model was developed to monitor learning progress achievement.