Background: School breakfast may contribute to increased risk for obesity because children may be consuming two breakfasts: at home and at school. The purpose of this study is to determine the prevalence of preschoolers consuming two breakfasts and to assess relationships with overweight/obesity and other factors. Method: Head Start parents (n = 273, 84.6% Hispanic) in the southwest completed cross-sectional surveys on child breakfast patterns and parental perceptions of school breakfast and personal breakfast consumption habits. Surveys were linked with sociodemographics and body mass index in Head Start databases in 2013. General estimating equation binomial models (schools as a random effect) were used to assess the relationship between two breakfasts (at home and school) and key variables, adjusting for gender, race, ethnicity, and household income. Results: The prevalence of consuming two breakfasts was 34%. Children's overweight/obesity status was inversely related to two-breakfast consumption, but it was significant only for the Hispanic subgroup; the odds of being overweight/obese was 60% lower among those who ate two breakfasts (p < 0.05). The likelihood of consuming a second breakfast increased over twofold among children who woke up before 7 a.m. (p = 0.004). Among Hispanic families, a significant association was observed between children's two-breakfast consumption and parental perceptions about whether they perceived the breakfast at Head Start was culturally appropriate (p = 0.040). Conclusions: Not only was eating two breakfast not associated with obesity, the association was in the opposite of the expected direction and significant for Hispanic participants. Factors such as earlier wake-up time were related to reports of two breakfast intake. While more research is needed, these findings provide information for policy makers and practitioners; caution should be exercised when suggesting that breakfast programs may be related to the consumption of two breakfasts and the risk for childhood obesity, particularly among the preschool students in this study.