Teacher assessments are often used alongside parent assessments to identify behavioral problems and patterns in school-aged children. These assessments can aid in the diagnosis of disruptive behavior disorders and are used to screen children for targeted delinquency prevention programs. Although researchers have heavily studied the relationship between parent and teacher assessments, not as much research has analyzed teacher assessments alone, specifically semiannual teacher assessments. Teacher assessments are typically conducted during the fall semester, normally a couple months into the school year, or during the spring semester, normally a couple months after the winter break period. Using data from the Pittsburgh Youth Study (PYS), we aimed to determine the temporal stability and predictive utility of semiannual teacher assessments of children's behavioral problems from 2nd grade to 5th grade. Results showed that mean assessment scores increased from the fall to the spring semester across all 4 grades. We also found that teacher assessments of behavioral problems in grade school were significantly correlated with future serious violence. Although our statistical model did not identify a specific time period or semester when these assessments were most predictive, we observed a pattern where the spring semesters were more predictive for the younger grades, and the fall semesters were more predictive for the older grades. Future research could aim to understand why this pattern exists and what its implications are.