Continental strike-slip shear zones that may bear important information about the evolution of convergent tectonics often occur to accommodate plate convergence. When and how shearing along the shear zones responds to plate interactions, however, are often debated. In this study, we investigated the Oligocene–Miocene leucocratic dikes from the Ailao Shan–Red River shear zone, which was active during India-Eurasia plate convergence, to constrain the timing and mechanism of ductile shearing along the shear zone. The dikes are structurally grouped into pre-, syn-, and postkinematic types with respect to ductile shearing. Prekinematic dikes from ca. 41 to 30 Ma have low whole-rock 87Sr/86Sr(i) values (0.707–0.710), generally high εNd(t) values (–3.31∼–7.98), and variable εHf(t) values (–7.9∼+5.7). Their magma sources involved high thermal perturbation inducing partial melting of the lower crust, and contributions from the mantle that were possibly related to extensional collapse of the orogenic belt prior to tectonic extrusion of the Sundaland block. Syn- and postkinematic dikes from ca. 28 to 20 Ma dominantly have high whole-rock 87Sr/86Sr(i) (0.707–0.725) and low εNd(t) (–5.83 to –9.76) values, and either negative or positive zircon εHf(t) values (broadly in the range of –12 to + 7.6) for coeval but separate crustal magma sources. The results imply that major shearing accompanying retrograde metamorphism along the Ailao Shan–Red River shear zone was localized to crustal level. A synthesis of regional structural data suggests that Oligocene–Miocene shearing along the Ailao Shan–Red River shear zone and lateral tectonic extrusion of the Sundaland block proceeded in response to progressive India-Eurasia plate convergence. Distributed and inhomogeneous middle- to lower-crustal flow along the boundaries of and within the Sundaland block occurred during the tectonic extrusion.