Cognitive self-regulation and the behavioral manifestations of cognitive self-regulation are important aspects of school readiness, yet less is known about the variation in measurement modalities within children. In this dissertation, two studies examined the makeup, antecedents, and consequents of constellations of cognitive self-regulation (CSR) measures around the transition to formal schooling. Study 1 explored how distinct profiles of multiple measurement modalities (direct assessments, maternal reports, and observer ratings) of CSR were associated with earlier individual child and familial factors. Person-centered analyses uncovered four multi-method CSR profiles in preschool at 54-months: (1) excellent regulators, with consistently high CSR across all measures; (2) good regulators, with slightly lower – but still good – CSR across all measures; (3) struggling regulators, with low CSR across all measures; and (4) inconsistent regulators, paralleling the struggling regulators profile in all measures except observer ratings. This last profile showed high CSR for both observer rating indicators. Three profiles capturing child CSR in 1st grade largely replicated preschool results with one exception: the excellent and good regulator profiles were not analytically distinguishable from one another, resulting in, (1) good regulator, (2) struggling regulator, and (3) inconsistent regulator profiles. Additionally, some child (cognitive functioning, gender) and familial (maternal vocabulary) factors were related to child CSR profiles at both time points. Further, mother-child attachment and better early home quality were related to more well-regulated CSR profiles prior to school entry only, whereas child minority status was significant only for 1st grade. Study 2 examined how children’s preschool and 1st grade CSR profiles were longitudinally related to academic and socioemotional outcomes in middle childhood and adolescence. Results indicated that a gradient of child CSR was associated with subsequent functioning in academic and socioemotional domains. Additionally, findings suggested that members of the inconsistent regulator profiles showed some lower internalizing behavior problems, as well as higher externalizing and lower academic performance in some comparisons. Some differences in preschool and 1st grade CSR profiles associations with middle childhood and adolescent outcomes were also found. Together, these studies provide a “proof of concept” that utilizing person-centered approaches to explore multiple measurement modalities of child CSR is feasible, and reveal a unique subgroup of children previously unexamined through variable-centered approaches alone.