This study investigated school connectedness, student engagement, academic grades, and student affect. Factor analyses of 331 adolescent students (Years 7, 9, and 11 in Australia), validated a four-factor model of school engagement. The factors revealed in the analyses were described as (1) future and task focus, (2) planning and motivation, (3) positive roles and models, and (4) positive social engagement. Cluster analyses revealed two typologies of students: a thriving group scoring significantly higher on all four factors than a striving group. There was a consistent number of students in each group across Years 7, 9 and 11. Compared to students in the striving group, on average, students in the thriving group scored significantly higher on grades (i.e., mathematics and English). Moreover, students in the thriving group were significantly higher on content and excited affects, and significantly less depressed and distressed compared to the students in the striving group. Limitations and implications for research and practice are discussed.