Particle Image Velocimetry (PIV) has been used to study the complex flowfield created by simulated battle damage to a two-dimensional wing. Computational Fluid Dynamics (CFD) predictions have also been used for validation of internal cavity flow. Two damage cases were selected for the study; both cases were simulated using a single hole with diameters equal to 20% and 40% of the chord, located at the wing half-chord. Wind-tunnel tests were conducted at a Reynolds number of 500,000 over a range of incidences from 0 to 10° with two-component PIV measurements made on three chordwise and three spanwise planes. The PIV data were analysed and compared to CFD data of the same damage cases. The PIV data have shown lower velocity ratios and lower vorticity in the jet compared to past Jet in Cross-Flow experiments and CFD was used to describe the flow features inside the cavity of the wing. It was seen that the wing cavity has large effects on the external flow features, particularly for the 20% damage case. Finally, the flow field data have been related to force balance data. At higher incidence angles, the larger force coefficient increments in both lift and drag can be attributed to the larger wakes and higher jet strengths.