To address the problem of low achieving math students, a cross-age math tutoring intervention paired middle school tutors with kindergarten and first grade students with low math skills. This instrumental group case study explored the effects of the intervention on the math skills of the students through teacher interviews and the testing program of "Aimsweb Plus" (Pearson, 2017) before and after the tutoring intervention. Most of the teachers of the tutees reported measurable math gains possibly from the tutoring and most of the teachers observed improved attitude towards math work for the young tutees. Most teachers of the tutors did not report any measurable math gain from tutoring young students. All the teachers of the tutors recommended the cross-age tutoring experience as the middle school students seemed to show increased leadership skills, confidence, or found helping others a positive experience.