Inter- and intraindividual differences in Finnish adolescents’ developmental trajectories of school engagement and burnout (exhaustion, inadequacy, and cynicism) and their associations with students’ concurrent progression in mathematics performance and educational aspirations were investigated in an accelerated longitudinal study design spanning ages 13–17 (N = 1131, 50.9% girls). Growth mixture modeling analyses identified four distinct trajectory profiles: Positive academic well-being (high and stable engagement, low and stable burnout), Negative academic well-being (low U-shaped engagement, increased burnout), Disengaged (low U-shaped engagement, but also low and stable burnout), and Declining academic well-being (declining but U-shaped engagement, increasing burnout). Most students experienced a positive change in their trajectories after entering upper secondary education. Furthermore, students in the Positive academic well-being group performed better and progressed faster in mathematics and reported higher educational aspirations. Students in the Declining academic well-being group started out with high performance and aspirations, but they progressed at a slower rate in mathematics and lowered their aspirations over time. The Disengaged students’ performance progressed at the slowest rate of all groups, and they had one of the lowest educational aspirations overall. Lastly, students in the Negative academic well-being group performed the lowest in mathematics, and had one of the lowest aspirations for future educational degrees.