The rearrangement of drainage basins provides critical insight into crustal deformation and geodynamic mechanisms. Near the southeastern boundary of the Tibetan Plateau, the Dadu River abruptly shifts from south- to east-flowing, providing important implications for regional tectonogeomorphic development since the mid-Pleistocene. South of the bend, the headwaters of the Anning River occupy an unusually wide valley. Field investigations show that large quantities of fluvial/lacustrine sediments are widespread along the Dadu and Anning rivers and are exposed at their drainage divide. Detrital zircon U-Pb age patterns confirm that these fluvial/lacustrine sediments are the remnants of the paleo-Dadu River, which strongly suggests that the paleo-Dadu River originally flowed southward into the Anning River. The cosmogenic nuclide burial ages of the lacustrine sediments along the Dadu and Anning rivers suggest deposition of these sediments from separate dammed lakes ca. 1.2 Ma ago, ca. 0.6 Ma ago, and ca. 0.9 Ma ago from north to south, respectively. Provenance and burial-age studies indicate that reorganization of the Dadu drainage occurred within the last 0.6 Ma. We propose that this drainage reorganization in southeastern Tibet resulted from progressive convergence between the India and Eurasian plates during the Pleistocene.