Multiyear teacher–student assignments, often known as “looping”, extend relationships among teachers, students, and families beyond a single school year. Using administrative data from a large urban district spanning more than a decade, we develop an empirical approach to identifying intentional looping and estimate its associations with student achievement in grades 4–8, distinguishing looping from incidental repeat teacher–student matches and separating intended from realized continuity. Within a fixed-effects framework that accounts for selection into and out of looping classes, results show that looping is uncommon but associated with gains of roughly 0.04–0.05 standard deviations in ELA and 0.025–0.04 in math—meaningfully larger than those associated with incidental repeat matches. Estimated associations are larger in middle-grade ELA and elementary math and remain robust to alternative model specifications and definitions.