High school students aspiring to become music educators (n = 116) and upper-level music education majors (n = 130) took part in this investigation comparing higher-order thinking skills in an observation analysis task. We used certain procedures from previous investigations (Sheldon & DeNardo, 2004; Standley & Madsen, 1991). Upperclassmen demonstrated greater higher-order thinking skills, measured by success in providing descriptive and inferential statements in an observation task, compared to prospective freshmen. This outcome is consistent with those of prior studies (Sheldon & DeNardo, 2004; Standley & Madsen, 1991) and suggests that the continued development of higher-order thinking skills among prospective music educators can be cultivated within an undergraduate music education degree program. When entrance examination variables of prospective freshmen were analyzed for relationships, few strong correlations were found.