Research investigating teachers’ and preservice teachers’ (PSTs) experiences delivering Sport Education (SE) necessitates further attention (Glotova & Hastie, 2014). Research that has been conducted to date has shared varied findings, with some teachers finding it difficult to teach SE in its entirety (Curtner-Smith, Hastie, & Kinchin, 2008). This study investigated seven PSTs’ delivery of SE during their teaching placement in the final year of their physical education teacher education (PETE) program. Data were gathered through pre- and postteaching placement interviews and midteaching placement focus groups, which were analyzed using thematic coding and constant comparison (Miles & Huberman, 1994; Thomas, 2009). Occupational socialization (Lawson, 1983a, 1983b) was used as the framework to analyze the factors that influenced their learning and delivery of SE. Findings show that PSTs encountered specific difficulties related to teaching SE on teaching placement and that their cooperating teachers played a significant role in their delivery of SE.