Youth leaving or being discharged from child protection services (CPS) are a particularly vulnerable population in Canada that could be at an increased risk of homelessness, which has many adverse consequences including declining physical and mental health, school disengagement, involvement with the justice system, and substance use disorders. In this paper, we examine the extent to which youth accessing homelessness services with a history of involvement with CPS differ from their peers who have not interacted with CPS using the 2019 Without a Home: The National Youth Homelessness Survey—which is by far the largest study ever administered in Canada on youth homelessness (n = 1375). This examination includes a diverse range of life circumstances and outcomes, including quality of life, relationships with friends and family, criminal records, education, and adverse childhood experiences (ACEs). Furthermore, controlling for demographic characteristics, we present risk factors that are likely to be correlated with youth homelessness, including ACEs and the CPS history, and conclude by discussing policy implications and proposing future research avenues.