The present connector press-fitting apparatus comprises a press-fitting head, a press-fitting block, a cylinder, a positional detector, a pin detector, and a controller. The press-fitting head comes into contact with the connector, and attaches to and detaches from this connector. The press-fitting block supports the press-fitting head elastically. The cylinder is capable of moving the press-fitting block freely in a vertical direction, lowers the press-fitting block, and press-fits pins of the connector into a printed board which is arranged at a press-fitting position. The positional detector detects the displacement of the press-fitting head. The pin detector detects at least one pin lead end part projecting below the printed board in accordance with the press-fitting operation of the connector by means of the cylinder. The controller detects when the press-fitting block is in a standard insertion position by means of the positional detector, and at the point in time at which the pin detector has detected at least one pin lead end part, the controller lowers the press-fitting block by means of the cylinder and press-fits the pin base end parts of the connector into the printed board.