Self-resonating waterjets (SRWJs) are being widely used in the fields of energy exploitation, due to the significantly increased penetration rate of roller bits in deep-hole drilling. To further improve the impact and erosion abilities of SRWJs, the effects of the downstream contraction ratio of organ-pipe nozzle on the axial pressure oscillations were experimentally studied. The axial pressure oscillation peak and amplitude were used to evaluate the effects under two inlet pressures and various standoff distances. The results show that the downstream contraction ratio can affect the development trends of the pressure oscillations and determines the values of the peaks and amplitudes. Under the experimental conditions, 2.5 is the ratio that leads to the maximum peaks and amplitudes at almost all the testing standoff distances, while the ratio of 2 always results in the minimum ones. The development trend of the pressure oscillation peak for the ratio of 3.5 has a great change at an inlet pressure of 20 MPa. Generally, the relative pressure oscillations are more violent at an inlet pressure of 10 MPa, which is regardless of the contraction ratio. This study helps provide a guideline for determining the physical parameters required in the fabrication of organ-pipe nozzles used for deep-hole drilling.