Low-income students are at increased risk for grade retention and suspension, which dampens their chances of high school graduation, college attendance, and future success. Drawing from a sample of 357 children and their families who participated in the Chicago School Readiness Project, we examine whether greater exposure to cumulative poverty-related risk from preschool through 5^th grade is associated with greater risk of student retention and suspension in 6^th grade. Logistic regression results indicate that exposure to higher levels of cumulative risk across the elementary school years is associated with students’ increased risk of retention in 6^th grade, even after controlling for child school readiness skills and other covariates. Importantly, findings of the association between average cumulative risk exposure and student suspension are more complex; the role of poverty-related risk is reduced to non-significance once early indicators of child school readiness and other covariates are included in regression models. While, children’s early externalizing behavior prior to kindergarten places children at greater risk of suspension 7 years later, children’s higher levels of internalizing behaviors and early math skills are associated with significantly decreased risk of suspension in the 6^th grade. Together, findings from the study suggest the complex ways that both early school readiness and subsequent exposure to poverty-related risk may both serve as compelling predictors of children’s likelihood of “staying on track” academically in the 6^th grade.