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Given the significance of teacher quality and the pressing need to address teacher shortages worldwide, this study examined the evolving landscape of adolescents’ teaching career expectations in the last two decades. The Programme for International Student Assessment data showed (a) the proportions of adolescents aspiring to teaching careers remained stable over the two decades with girls in dominance; (b) boys with higher reading and science achievement aspired to teaching careers more; (c) girls expected to become teachers regardless of socio-economic background, while its impact on boys varied in different economies; and (d) boys required enjoyment of reading, self-efficacy, and environmental support for choosing teaching careers, whereas girls were naturally inclined to be teachers.