Early life experiences and the process of exploration play a vital role in shaping brain development and lifelong learning. In March 2020, population-wide restrictions were imposed due to the COVID-19 pandemic. It remains to be determined whether having been raised under the global stress and restrictions of COVID-19 has influenced children’s development as they enter formal schooling. The aim of this study was to examine the extent to which having more than 50% of one’s first year of life and/or prenatal period in the COVID-19 era influences the developmental trajectory in preschool. The study compared 3-to 5-year-old children born before the pandemic (n = 63) with those who were five months or younger at its onset (n = 40). Variables assessed included executive function skills, vocabulary, and common developmental domains. Using the BRIEF-P as a standardized measure of executive function, the results demonstrate that, the pandem-ic-born cohort exhibit greater impairments than those born before the pandemic. There was also a significant increase in reports of speech and language therapy enrollment; frequent ear infections; diagnoses of hearing, speech, or language impairments; and delays in reaching developmental milestones. The pandemic-born cohort additionally reported delays in fine motor skills compared to the pre-pandemic cohort. The present study underscores the urgent need for additional resources to better support children in this cohort as they begin formal schooling.