Students’ emotions (e.g., enjoyment, boredom) while doing math and their situational interest in mathematics are important for their learning of mathematics, but examinations of teachers’ judgments of students’ emotions and interest while solving tasks are rare. Moreover, we do not know much about the predictors of teachers’ judgments of students’ emotions and interest. In this study, we addressed preservice teachers’ judgments of students’ task-specific enjoyment, boredom, and situational interest and analyzed whether such judgments are related to preservice teachers’ own enjoyment, boredom, and interest. Furthermore, we aimed to analyze whether preservice teachers’ judgments differ between the two types of tasks under investigation (tasks with and without a connection to reality). To achieve these aims, 182 preservice teachers were randomly assigned to one of two study conditions. In one condition, preservice teachers' judgments of task-specific emotions and situational interest for fictitious 9th-grade students were measured, and in the second condition, preservice teachers' own task-specific emotions and situational interest were measured. The results show that preservice teachers' judgments of students’ task-specific emotions and situational interest differ for tasks with and without a connection to reality. Further, our findings indicate that preservice teachers’ judgments of students’ task-specific emotions and interest differ from preservice teachers' own task-specific emotions and interest. Implications for theoretical models of teachers’ judgments and consequences for teacher education are discussed.