This paper presents an experimental investigation of the aerothermal performance of a cooled winglet tip under transonic conditions (exit Mach number of 1.0, and an exit Reynolds number of 1.27 × 106, based on axial chord). Spatially resolved heat transfer data and film cooling effectiveness data are obtained using the transient infrared thermography technique in the Oxford High-Speed Linear Cascade test facility. Aerodynamic loss data are obtained by traversing a specially made and calibrated three-hole pressure probe and a single-hole probe one axial chord downstream of the blade. Detailed contours of Nusselt number show that for an increase in tip clearance, with and without film cooling, and for coolant injection, for both tip clearances, the Nusselt number increases. Also the smaller tip clearance observes higher film cooling effectiveness overall. Detailed distributions of kinetic energy losses as well as pitch-wise averaged loss coefficients and loss coefficients at a mixed-out plane indicate that the size of the loss core associated with the over-tip leakage vortex decreases with cooling injection.