Numerosity estimation performance (e.g., how accurate, consistent, or proportionally spaced (linear) numerosity-numeral mappings are) has previously been associated with math competence. However, the specific mechanisms that underlie such a relation is unknown. One possible mechanism is the mapping process between numerical sets and symbolic numbers (e.g., Arabic numerals). The current study examined two hypothesized mechanisms of numerosity-numeral mappings (item-based “associative” and holistic “structural” mapping) and their roles in the estimation-and-math relation. Specifically, mappings for small numbers (e.g., 1–10) are thought to be associative and resistant to calibration (e.g., feedback on accuracy of estimates), whereas holistic “structural” mapping for larger numbers (e.g., beyond 10) may be supported by flexibly aligning a numeral “response grid” (akin to a ruler) to an analog “mental number line” upon calibration. In 57 adults, we used pre- and post-calibration estimates to measure the range of continuous associative mappings among small numbers (e.g., a base range of associative mappings from 1 to 10), and obtained measures of math competence and delayed multiple-choice strategy reports. Consistent with previous research, uncalibrated estimation performance correlated with calculation competence, controlling for reading fluency and working memory. However, having a higher base range of associative mappings was not related to estimation performance or any math competence measures. Critically, discontinuity in calibration effects was typical at the individual level, which calls into question the nature of “holistic structural mapping”. A parsimonious explanation to integrate previous and current findings is that estimation performance is likely optimized by dynamically constructing numerosity-numeral mappings through the use of multiple strategies from trial to trial.