ABSTRACT Middle school is a time of transition associated with increases in peer victimization (PV) and stress that warrant additional attention. Middle school students (N = 256; 54.7% male; M age = 12.24, SD age = .94) completed measures of PV, negative life events (NLEs), anxiety, and depression. Students were assessed across 6 time points to examine if PV and the number of NLEs at baseline (Time 1; T1) had a unique and interactive effect on symptoms of depression and anxiety concurrently and over three school years. Results suggest that T1 PV, T1 NLEs, and their interactions were significantly associated with concurrent depression. Moreover, the association between T1 PV and the trajectory of depression was moderated by T1 NLEs. Associations with anxiety were not as substantial; nonetheless, T1 PV was significantly associated with concurrent anxiety. Findings clarify the cross-sectional and longitudinal association between PV and NLEs on internalizing symptoms in middle school with an emphasis on the substantial risk of depression symptomatology.