The invention provides a conical pin size measuring device and a measuring method. The conical pin size measuring device comprises a reference block, reference holes and a distance measuring device. When the measuring device is used, a conical pin is placed into two groups of reference holes and perpendicular to a reference plane, the hole diameter of each reference hole is positioned between the diameter of a large end and the diameter of a small end of the conical pin to be measured, the conical pin to be measured is placed into a first reference hole and a second reference hole, the small end of the conical pin to be measured enters the reference holes, the large end of the conical pin to be measured does not enter the reference holes, the diameter of the first reference hole is A1, and the diameter of the second reference hole is A2. When the conical pin to be measured in the reference holes is measured by the aid of a depth indicator, the distances B1 and B2 between the large end face of the conical pin and the reference surface are measured by a depth gauge when the conical pin is placed in the two reference holes, and finally, the taper and the diameter of the large end of the conical pin are calculated. According to the device, measuring processes are simpler and more convenient, the size of a nonstandard conical pin can be simply, conveniently, rapidly and accurately measured, and the device has the advantages of simple structure, convenience in use, high practicability, easiness in popularization and the like.