Children with Attention Deficit/Hyperactivity Disorder (ADHD) receive approximately 80% of instruction in the general education classroom, where individualized behavioral management strategies may be difficult for teachers to consistently deliver. Mobile device apps provide promising platforms to manage behavior. This pilot study evaluated the utility of a web-based application (iSelfControl) designed to support classroom behavior management. iSelfControl prompted students every 'Center' (30-minutes) to self-evaluate using a universal token-economy classroom management system focused on compliance, productivity, and positive relationships. Simultaneously, the teacher evaluated each student on a separate iPad. Using Multi Level Modeling, we examined 13 days of data gathered from implementation with 5th grade students (N = 12) at a school for children with ADHD and related executive function difficulties. First, an unconditional growth model evaluated the overall amount of change in aggregated scores over time as well as the degree of systematic variation in scores within and across teacher-student dyads. Second, separate intercepts and slopes were estimated for teacher and student to estimate degree of congruency between trajectories. Finally, differences between teacher and student scores were tested at each time-point in separate models to examine unique 'Center' effects. 51% of the total variance in scores was attributed to differences between dyads. Trajectories of student and teacher scores remained relatively stable across seven time-points each day and did not statistically differ from each other. On any given day, students tended to evaluate their behaviors more positively (entered higher scores for themselves) compared to corresponding teacher scores. In summary, iSelfControl provides a platform for self and teacher evaluation that is an important adjunct to conventional classroom management strategies. The application captured teacher/student discrepancies and significant variations across the day. Future research with a larger, clinically diagnosed sample in multiple classrooms is needed to assess generalizability to a wider variety of classroom settings.