This study examines how the discriminatory practices and racism in the education system contribute to the low achievement and high dropout rate of Somali-Canadian youth. Through qualitative research, semi-structured interviews with nine participants--this study explores the educational experiences of Somali students in the Toronto District School Board (the TDSB). This study found Somali students experience systemic discrimination in local TDSB schools--unfair grading practices, ethnic grading, differential treatment, deliberate streaming, stereotyping, profiling, the unequal application of discipline policies, disproportionate rates of suspensions and lack of religious accommodation. This study also found that systemic discrimination contributes to low achievement of Somali students, their disengagement from learning process, early school departure, and the criminalization of Somali boys. This study employs Critical Race Theory (CRT) in education as its main theoretical framework, through this lens the researcher links the schooling problems of Somali students to systemic discrimination based on their race and/or ethnicity.