Direct Behavior Rating-Single Item Scales (DBR-SIS) have been advanced as a promising, systematic, behavioral, progress-monitoring method that is flexible, efficient, and defensible. This study aimed to extend existing literature on the use of DBR-SIS in elementary and secondary settings, and to examine methods of monitoring student progress in response to intervention. To this end, two concurrent multiple baseline design studies were conducted in a diverse magnet school district located in the northeastern United States. One study was conducted with four students in kindergarten and first grade, whereas the second study was conducted with three students in 10th and 11th grade. Response to a Daily Report Card (DRC) intervention was monitored using two different approaches: DBR-SIS and systematic direct observation (SDO) probes. Across all participants, modest improvements in behavior were observed using both visual and quantitative analyses of DBR-SIS data; however, decisions regarding student response to the intervention varied as a function of the dependent variable analyzed. Implications for practice and future directions for research are discussed.