There is ongoing debate regarding what performance on the number line estimation task represents and its role in mathematics learning. The patterns followed by children’s estimates on the number line task could provide insight into this. This study investigates children’s estimation patterns on the number line task and assesses whether mathematics achievement is associated with these estimation patterns. Singaporean children (n = 324, Age M = 6.2 years, Age SD = 0.3 years) in their second year of kindergarten were assessed on the number line task (0-100) and their mathematical performance (Numerical Operations and Mathematical Reasoning subtests from WIAT II). The results show that most children’s number line estimation patterns can be explained by at least one mathematical model (i.e., linear, logarithmic, unbounded power model, one-cycle power model, two-cycle power model). But the findings also highlight the high percentage of participants for which more than one model shows similar support. Children’s mathematical achievement differed based on the models that best explained children’s estimation patterns. Children whose estimation patterns corresponded to a more advanced model tended to show higher mathematical achievement. Limitations of drawing conclusions regarding what performance on the number line task represents based on models that best explain the estimation patterns are discussed.