Children involved in child welfare experience academic difficulties more than any other functioning concern. This study used data from OIS-2013, a large representative sample of child welfare investigations (n = 4033), involving children aged 4–15. The following research questions were answered: 1) Do children with maltreatment histories and academic difficulties differ from those with maltreatment histories but no academic difficulties; and 2) Does the presence of academic difficulties influence ongoing child welfare services. Frequencies, cross-tabulations, and Chi-square tests assessed the relationships between academic difficulties and child characteristics, caregiver functioning concerns household characteristics, and maltreatment. Transfer to ongoing child welfare services was the outcome variable in a multiple logistic regression analysis. Being an adolescent, male, Indigenous, and having additional child functioning issues, notably externalizing behaviour, suicidal thoughts, and self-harm were each related to academic difficulties. Academic difficulties were significantly related to households where a caregiver had a cognitive impairment or low social supports, that were overcrowded, unsafe, or of lower income. Children who have academic difficulties are more likely to have recurrent involvement in child welfare, significant risk of future maltreatment, to experience physical harm, and to be placed in out of home care. Unsafe housing was the most significant predictor of a decision to transfer a case to child welfare services, followed by caregiver functioning, maltreatment type, then academic difficulties, when controlling for child gender, age, and ethnicity. Difficulties are likely to compound over time, and ultimately increase cost and frustration across systems.