This study investigated differences in difficulty among three types of math board games used as curricular materials in some preschool classrooms. Difference in performance between low- and middle-income children on the three types of games was also explored. Children drew cards containing one to five large dots; they then attempted to place an equivalent number of counters on a bingo-type board or move an equivalent number of spaces along a short or a long path. The sample consisted of 86 children of diverse race/ethnicity and socioeconomic status, age 3 to 5 years, enrolled in a licensed, urban preschool in the Midwest United States. A mixed-methods design was employed. Repeated measures ANOVA and post hoc testing showed that children scored significantly higher (p < 0.0001) on grid and short-path games than on longer path games. Head Start children scored significantly lower than middle-income children at age 3, but not at age 4 or 5. Qualitative data revealed mathematical behaviors that indicate when a child is ready to move to a more difficult level of game, as well as common error sources on long-path games.