In this qualitative article, we argue that marginalized spaces in historically disadvantaged school settings, such as in the case of a marginalized group of people, an out-group in the South African society, can become counter-spaces of comfort and nurturance. Spaces in historically disadvantaged communities are usually perceived in the dominant discourse as locations of deficiencies. We use Critical Race Theory and Latina/Latino Critical Theory framework (CRT and LatCrit) to contest dominant ideologies; especially the historically disadvantaged who often display human agency and transformational resistance. In addition, through the framework of Edupreneurial leadership theory we set out to explore how school practices incorporate cultural forms of knowledge, balancing the external and internal functions of the school to realize a conducive environment for effective school development. Fifteen participants were chosen through purposeful sampling and snowballing from five different schools in the Western Cape province of South Africa. Semi-structured interviews were used to generate data from different sets of participants; then analyzed where various themes crystallized responding to the research questions. The findings foreground the way in which historically disadvantaged learners' home lives, community initiatives and particular school practices lead strategies of resistance to challenge oppressive structures.