ABSTRACT Using the data extracted from Macao-Data-PISA 2003, the present study explored the relationships of family structure, students’ SES, and grade retention to the educational and occupational expectations of the 15-year-old high school students (n=1250) in Macao. This study examined the correlations of the variables in the circumstance of Macao. The ultimate goal of the study is to seek factors having impacts on students’ future choices for education and career in order to build reference for career guidance and counseling of local students. The findings of the study indicated that there was no significant relationship between family structure and the expectations whereas there were significant relationships found between students’ SES and the expectations and significant negative relationships found between grade retention and the expectations. Ordinal logistic regression data analysis techniques were utilized to determine the role of predictor variables to educational expectation. As the relationships of students’ SES and grade retention to the expectations were revealed, suggestions made for the prevention and intervention career counseling programs in school were made. The understandings of the influencing factors enable teachers and school counselors to provide appropriate supports to needed students. Keywords: SES, grade retention, family structure, educational expectations, occupational expectations, career guidance.