Discrepancies between teacher and parent reports of children’s externalizing behaviors are well documented. However, less research has examined the associations these different ratings have with objective indicators of functioning in other domains. The goal of this study was to compare the strength of association of parent and teacher reports of externalizing behaviors with children’s early academic skills. The sample consisted of 695 children (376 boys, 318 girls, 1 unknown) who ranged between 48 months and 63 months of age (mean age = 55.05; SD = 3.63) at time of initial assessment. Children completed standardized measures of early academic skills; parents and teachers completed the Conners Rating Scale. Steiger’s Z tests were performed to compare the strength of associations between parent and teacher ratings on children’s early academic skills. Multi-level regressions examined the unique predictive variance each rater accounted for. Teacher ratings of inattentive and oppositional defiant behaviors had stronger associations with children’s early academic skills than did parent ratings for most measures of early academic skills, but there were no significant differences for ratings of hyperactive/impulsive behaviors. Multivariate analyses revealed that only teacher ratings of inattentive behaviors accounted for notable portions of unique variance in early academic skills. Children’s externalizing behaviors were related to their early academic skills. However, these results suggest that teachers contributed more unique variance, possibly due to their access to a normative reference group.