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Importance: Children born preterm may experience learning challenges at school. However, there is a paucity of data on the school readiness of these children as they prepare to begin grade 1., Objective: To examine the association between prematurity and school readiness in a population-based cohort of children., Design, Setting, and Participants: This cohort study was conducted in the province of Manitoba, Canada, and involved 2 cohorts of children in kindergarten at the time of data collection. The population-based cohort included children born between January 1, 2000, and December 31, 2011, whose school readiness was assessed in kindergarten using the Early Development Instrument (EDI) data. The sibling cohort comprised children born preterm and their closest-in-age siblings born full term. Data were analyzed between March 12 and September 28, 2021., Exposures: Preterm birth, defined as gestational age (GA) less than 37 weeks., Main Outcomes and Measures: The primary outcome was vulnerability in the EDI, defined as a score below the tenth percentile of the Canadian population norms for any 1 or more of the 5 EDI domains (physical health and well-being, social competence, emotional maturity, language and cognitive development, and communication skills and general knowledge). Logistic regression models were used to identify the factors associated with vulnerability in the EDI. P values were adjusted for multiplicity using the Simes false discovery method., Results: Of 86 829 eligible children, 63 277 were included, of whom 4352 were preterm (mean [SD] GA, 34 [2] weeks; 2315 boys [53%]) and 58 925 were full term (mean [SD] GA, 39 (1) weeks; 29 885 boys [51%]). Overall, 35% of children (1536 of 4352) born preterm were vulnerable in the EDI compared with 28% of children (16 449 of 58 925) born full term (adjusted odds ratio [AOR], 1.32; 95% CI, 1.23-1.41; P < .001]). Compared with children born full term, those born preterm had a higher percentage of vulnerability in each of the 5 EDI domains. In the population-based cohort, prematurity (34-36 weeks' GA: AOR, 1.23 [95% CI, 1.14-1.33]; <34 weeks' GA: AOR, 1.72 [95% CI, 1.48-1.99]), male sex (AOR, 2.24; 95% CI, 2.16-2.33), small for gestational age (AOR, 1.31; 95% CI, 1.23-1.40), and various maternal medical and sociodemographic factors were associated with EDI vulnerability. In the sibling cohort, EDI outcomes were similar for both children born preterm and their siblings born full term except for the communication skills and general knowledge domain (AOR, 1.39; 95% CI, 1.07-1.80) and Multiple Challenge Index (AOR, 1.43; 95% CI, 1.06-1.92), whereas male sex (AOR, 2.19; 95% CI, 1.62-2.96) and maternal age at delivery (AOR, 1.53; 95% CI, 1.38-1.70) were associated with EDI vulnerability., Conclusions and Relevance: Results of this study suggest that, in a population-based cohort, children born preterm had a lower school-readiness rate than children born full term, but this difference was not observed in the sibling cohort. Child and maternal factors were associated with lack of school readiness among this population-based cohort.