A pressure-sensitive paint (PSP) technique was applied in a wind tunnel experiment in the NASA Langley Research Center 8-Foot Transonic Pressure Tunnel to quantify the effect of wing fillets on the global vortex-induced surface static pressure field about a sharp leading-edge 76o/40o double delta wing, or strake-wing, model at subsonic and transonic speeds. Global calibrations of the PSP were obtained at M = 0.50, 0.70, 0.85, 0.95, and 1.20, a Reynolds number per unit length of 2.0 million, and angles of attack from 10 degrees to 20 degrees using an in-situ method featuring the simultaneous acquisition of electronically-scanned pressures (ESP) at discrete locations on the model. The mean error in the PSP measurements relative to the ESP data was approximately 2 percent or less at M = 0.50 to 0.85 but increased to several percent at M =0.95 and 1.20. The PSP pressure distributions and pseudo-colored planform view pressure maps clearly revealed the vortex-induced pressure signatures at all Mach numbers and angles of attack. Small fillets having a parabolic or diamond planform situated at the strake-wing intersection were designed to manipulate the vortical flows by, respectively, removing the leading-edge discontinuity or introducing additional discontinuities. The fillets caused global changes in the vortex-dominated surface pressure field that were effectively captured in the PSP measurements. The vortex surface pressure signatures were compared to available off-surface vortex cross-flow structures obtained using a laser vapor screen (LVS) flow visualization technique. The fillet effects on the PSP pressure distributions and the observed leading-edge vortex flow characteristics were consistent with the trends in the measured lift, drag, and pitching moment coefficients.