Pilot check valves were developed for use in crawler cranes, and the cracking pressure, which is a performance characteristic, was evaluated. A pilot check valve is a type of check valve that passes hydraulic oil in one direction and shuts it off in the reverse direction. The valve opens the poppet under the action of pilot pressure and passes hydraulic oil in the reverse direction. The main parts of the pilot check valve were a valve body, spool, retainer, poppet, seat, and spring. The verification of parts, the assembly, and the operating pressure were tested to evaluate the cracking pressure of the pilot check valve. The pressure acting on the pilot check valve increases the supply pressure according to the conditions of the spool and poppet so that it can be understood intuitively as well as through test results. The results of the optimized cracking pressure and working pressure were confirmed through pressure, oil leak, and operational tests. The effectiveness of the prototype was verified by confirming that the cracking pressure was 0.6 ± 0.05 MPa. The results of this study can be used as a basis for designing pilot check valves and evaluating the cracking pressures of various pilot check valves.