The role of play in early elementary education (K-2) generates dichotomous opinions, and more research is required to support efficacious pedagogical decision-making. This pilot study explored the effects of pedagogical approaches on Title I kindergarten students’ executive function (EF) to test the hypothesis that children, especially those from low socioeconomic backgrounds, will show greater gains in EF, reading, and math achievement when purposeful play is incorporated into learning. Students in the play-based group had statistically significantly stronger EF health than children in the contemporary group per teacher reports, and parents in the contemporary group were more concerned about children’s EF skills than those in the play-based group, although this was not statistically significant. Students in the play-based group had greater reading gains than students in the contemporary group. There were no statistically significant differences between classrooms in math growth, but there was a moderate effect size. The greater the teacher’s level of concern about students’ EF skills, the lower a child’s reading and math gains tended to be. Parent observations of children’s EF were not correlated to any measure. Despite some study limitations, the findings encourage continued exploration of play-based pedagogy to increase children’s EF skills and academic achievement outcomes.