Cognition plays an important role in language teacher decision-making. A number of sources, including schooling, influence the cognition of language teachers. The concept of schooling is identified as the history of teachers' own personal education influences on the teachers' knowledge, also referred to as apprenticeship of observation (AO). Through further conceptualization of schooling/AO involving the notion of history-in-person, the current multiple case study explored the prior learning experience of two Bangladeshi novice teachers of English: Kamrul and Monabbir (pseudonym), and how these experiences influenced their cognition of language. The findings suggest that the prior learning experience of English teachers has influenced their cognition and has taken on distinctive trajectories. Both AO and anti-apprenticeship of observation (anti-AO) were documented on the basis of the positive and negative English learning experiences of Kamrul and Monabbir at school. The article concludes with the implication of schooling in shaping the knowledge of language teachers and developing a context-based teacher education program.