Gap wind jets (Tehuano winds) trigger supersquirts of colder water and mesoscale asymmetric dipoles in the Gulf of Tehuantepec (GT). However, the effects of successive gap wind jets on dipoles and their effects inside eddies have not yet been studied. Based on the wind fields, geostrophic currents, and surface drifter dispersion, this research documented three dipoles triggered and modified by Tehuano winds. Once a dipole develops, successive gap wind jets strengthen the vortices, and the anticyclonic eddy migrates southwestward while the cyclonic eddy is maintained on the east side of the GT. During the wind relaxation stage, the cyclonic eddy may propagate westward, but due to the subsequent re-intensification of the Tehuano winds, the vortex could break down, as was suggested by surface drifter dispersion pattern and geostrophic field data. The effect of the Tehuano winds was evaluating via eddy-Ekman pumping. Under Tehuano wind conditions, Ekman downwelling (upwelling) inside the anticyclonic (cyclonic) eddies may reach ~ -2.0 (0.5) m d-1 and decrease as the wind weakens. In the absence of Tehuano winds, Ekman downwelling inside the anticyclonic eddy was ~ 0.1 (-0.1) m d-1. The asymmetry of downwelling and upwelling inside eddies during Tehuano wind events may be associated with Tehuano wind forcing.