A line of research has supported the development and validation of Direct Behavior Rating--Single Item Scales (DBR-SIS) for use in progress monitoring. Yet, this research was largely conducted within the general education setting with typically developing children. It is unknown whether the tool may be defensibly used with students exhibiting more substantial concerns, including students with social competence difficulties. The purpose of this investigation was to examine the concurrent validity of DBR-SIS in a middle school sample of students exhibiting substantial social competence concerns (n = 58). Students were assessed using both DBR-SIS and systematic direct observation (SDO) across three target behaviors. Each student was enrolled in one of two interventions: the Social Competence Intervention or a business-as-usual control condition. Students were assessed across three time points, including baseline, mid-intervention, and postintervention. A review of across-time correlations indicated small to moderate correlations between DBR-SIS and SDO data (r = 0.25-0.45). Results further suggested that the relationships between DBR-SIS and SDO targets were small to large at baseline. Correlations attenuated over time, though differences across time points were not statistically significant. This was with the exception of academic engagement correlations, which remained moderate-high across all time points.