Although in recent years there has been growing attention on how preservice classroom teachers (PCTs) learn to teach physical education (PE), it is still unclear if there are differences between PCTs who choose a PE specialization and those who do not. Investigating such differences could provide insights about the potential role of a PE specialization in PCTs’ learning. In this context, the purpose of this study was to explore the views and experiences of teaching PE of two groups of PCTs—one with a PE specialization and another without—during their student teaching. Data gathered through semi-structured interviews with 14 Cypriot PCTs, seven with a PE specialization and seven with no such specialization, were analyzed inductively. Although this analysis yielded similarities in the participants’ views on motor, cognitive, and affective domains, notable differences were also identified between participants’ views. PCTs in the PE specialization group emphasized more the correct performance and application of skills in games, seemed to feel more confident regarding their practices in teaching PE, and were largely concerned with the content being appropriate to students’ level. Conversely, participants in the no-specialization group raised more concerns about the task selection, sequencing, and time allocation. To the extent these differences are related to PCTs’ specialization, we suggest that a PE pathway be developed as a choice in teacher education. Alternatively, if this is not feasible, the study findings suggest that PCTs should at least be provided with opportunities to take more PE courses.