<p>Students commonly report increased levels of school-related stress that are related to various academic and psycho-emotional outcomes. The development of such stress is associated with students’ experiences of external school-related stressors such as achievement evaluations and grades. At the same time, findings on the interplay of stress and achievement are ambiguous, and reciprocal effects might be assumed. In addition, intrinsic efforts and orientations of students might further reinforce the individual perception of stress as well as the development of learning outcomes and moderate the association of school-related stress and academic achievement. One such personal value might be seen in students’ individual achievement orientation. Longitudinal insights into associations of school-related stress, academic achievement, and achievement orientations are lacking. The present paper addresses this desideratum and applies a three-wave survey to investigate the autoregressive and cross-lagged associations of school-related stress and academic achievement of <i>N</i> = 644 students. The results of (multigroup) cross-lagged panel models highlight significant autoregressive effects of school-related stress and academic achievement as well as cross-lagged effects of stress on achievement. No cross-lagged effects of achievement on stress became clear. Furthermore, the results indicate distinct relationships when differentiating between students with different levels of achievement orientation. In contrast to students with low or average achievement orientation, no significant stress–achievement link could be described in students with higher achievement orientation. Differences between groups were nonsignificant.</p>