Three experiments examined students’ calibration in physical education in relation to task characteristics. Participants in the 3 experiments were 388 students. Calibration accuracy and bias were calculated based on students’ predicted and actual performance in tests including variations of a sport task (basketball shooting) and tasks from different sports (basketball and soccer). An overconfidence effect was found in all experiments, and evidence regarding the hard–easy effect emerged. High compared with low performers were more accurate, and some variations with respect to gender also emerged. The magnitude of calibration error was similar across tasks, whereas approximately half of the students were consistent in the direction of calibration (most of them were overestimators). Results are discussed with reference to theoretical and empirical evidence associated with performance calibration and self-regulated learning in physical education. Methodological issues, practical implications, and future directions are also discussed.