To provide a drilling machine and a press fitting machine which are excellent in drilling efficiency, and reduce the damage of digging claws thereof.

The drilling machine includes a digging head 30 consisting of a peripheral head 31 and a central head 32 provided at the center of the peripheral head 31, wherein the peripheral head 31 and the central head 32 are each rotatable independently, and are vertically movable. The peripheral head 31 is connected to a hollow central tube 23, and the central head 32 is connected to the central shaft 25 passing through the central tube 23. The drilling machine includes: a first driving device 43 for rotating the central tube 23; a first cylinder 42 for moving the central tube 23 vertically; a second driving device 45 for rotating the central shaft 25; and a second cylinder 44 for moving the central shaft 25 vertically.