The cold expansion method is one of the most popular techniques in the fatigue enhancement processes, and it has been widely used as a means of improving the fatigue resistance for aircraft structures with holes. Cold expanded holes have lower compressive residual stresses on the entry surface rather than the middle and exit surfaces. Due to the nonuniform residual stress distribution, fatigue crack initiation often occurs on the entry surface. This study proposes a new approach to increase the compressive residual stress magnitude at the entry of the hole. The new method is to apply chamfers into holes before the cold expansion process. Split mandrel process was used to cold work the hole with and without chamfers. Both numerical and experimental studies were done to verify the effects of hole chamfers on the residual stress distribution of the cold expanded holes. Finite element analysis (FEA) was conducted in order to see the effects of the chamfer geometries on the residual stress distributions. The FEA results showed an improvement of compressive residual stress magnitudes at the entry position of the cold expanded hole. The numerical results were compared with X-ray diffraction measurements. Fatigue tests were done to compare the fatigue life of the holes with various chamfer sizes and angles. The cold expansion chamfered holes showed a clear improvement in fatigue life over cold expanded holes without chamfers.