The aim of this study was to examine the vocational outcome expectations of high school students. The vocational outcome expectations refer to the beliefs of an individual that certain behaviour will lead to desired vocational outcome, and it is measured by the Vocational Outcome Expectations Scale-Revised (VOE-R). The 529 high school graduates from Zagreb and its surroundings participated in the research. The data were collected online as a part of the research project Vocational Development in Adolescence: Setting the Adolescent Career Transition Model. The results confirmed the unifactorial structure of Vocational Outcome Expectations Scale-Revised and high reliability (α=.86). Using the results of hierarchical regression analysis, a 45.1% of variance of vocational outcome expectations can be explained by four blocks of predictors. Blocks of predictors used in regression analysis are demographic data, school context, environmental and personal strength, and professional predispozitions and goals. The best predictors of vocational outcome expectations are career maturity (β=.43), the core self-evaluation (β=.21), and leadership aspirations (β=.13). Possible implications of research results are discussed and suggestions for further research are given.