This study originates from the recognition that the learners of History at the Advanced Level of education in secondary schools attach less value to its undertaking regarding eventual career development. This challenge is attributed to among other reasons, limited integration of career guidance in the teaching of History at the Advanced Level of education in secondary schools. Russen’s theory of Historiography was employed to underpin the study. Thus, the study is guided by three research questions: firstly: What are the papers of History that are taught at the Advanced Level of education in secondary schools in Wakiso district that promote career development? Secondly, how is career guidance integrated into the teaching of History at the Advanced Level of education in secondary schools in Wakiso district? Thirdly how does the integration of career guidance in the teaching of History at the Advanced Level of education in secondary schools in Wakiso district promote career development? The study employed the qualitative approach, the interpretivism paradigm, and a multiple case study design. Data from questionnaires, interviews, and observations were thematically analyzed. The study findings revealed that career guidance principles are not integrated into the teaching of History at the Advanced Level of education leading to the attainment of theoretical skills. The contribution of this research lies in the teacher’s continuously combining career guidance principles with History content to enhance career development. In addition, the theoretical contribution of this study advocates for teachers and respective career counselors to supplement the constructs of Russe’s’ theory of historiography with “guided” to enable the learners of History to make informed career choices, attainment, and sustainability.