The achievement of laminar flow in the boundary layer at high-speed cruise conditions may further, in addition to shock-wave control, reduce the drag and extend the range of military fighter aircraft. To this end, a further investigation on transitional boundary-layer flow of fighter wings is needed due to different configurations from the wings used on conventional transport aircraft. In this paper, wind tunnel experiments and numerical simulations were conducted on three-dimensional transition of thin diamond-shaped wings used on advanced fighter aircraft at tran/supersonic design points. A newly proposed correlation of crossflow transition which includes the effect of surface roughness was introduced into the γ-Reθt transition model. Predicted results were in good agreement with flow visualizations. Results showed that the strength of the crossflow component grew rapidly around the leading edge because of the severe flow acceleration, just as the same as wings with a large aspect ratio. However, there seemed no regular pattern of instability-dominance variation in span-wise for a diamond configuration. The dominance of different instability mechanisms strongly depended on the local pressure distribution. Hereby, the research recommended a “roof-like” shape of pressure distribution to suppress both crossflow and Tollmien-Schlichting (T-S) instabilities. Besides, a sharp suction peak with a serious pressure rise should be cut off to avoid stronger instabilities. Further discussions also revealed an independence of the unit Reynolds number when transition was triggered by T-S instabilities. Aerodynamic force comparisons indicated that further benefit on drag reduction could be expected by including the three-dimensional transition effect into a wing design process.