Few studies have sought to understand the childhood play experiences of Black boys in early childhood education (ECE), and a majority of those that investigate them often socially construct Black boys' play as criminal, dangerous, and monstrous. Considering the dangers of hegemonic masculinity and femininity or the racial and gendered power and privilege White boys and girls bring to societal spaces including playgrounds, little is known about how such power influences the experiences of Black boys who play with them. In this conceptual paper, I draw on critical race theory (CRT) to trouble the criminalization of Black boys' childhood play and hegemonic White masculinity and femininity, which can prove violent and dehumanizing to Black boys. As such, I suggest that similar to the school-to-prison pipeline (STPP), Black boys may become victims of what I call the "school playground-to-prison pipeline (SPTPP)" as a consequence of White children's accusations, fears, misperceptions, and misreadings of Black boys' play. Recommendations are provided for teacher and ECE to better support Black boys and the cross-cultural play interactions between them and White children.